Compound for organic electric element, organic electric element comprising the same, and electronic device thereof

ABSTRACT

Provided are a compound represented by Formula 1, an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and an electronic device thereof, wherein by comprising compound represented by Formula 1 in the organic material layer, the driving voltage of the organic electric element can be lowered, and the luminous efficiency and life time, in particular, life time can be improved.

BACKGROUND Technical Field

The present invention relates to a compound for an organic electricelement, an organic electric element comprising the same and anelectronic device thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer has a multi-layered structure havingrespectively different materials in order to improve efficiency andstability of an organic electric element, and for example, may include ahole injection layer, a hole transport layer, a light emitting layer, anelectron transport layer, an electron injection layer, or the like.

The most important issues in organic electroluminescent element are lifeand efficiency, and as the display becomes larger, these efficiency andlife problems must be solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase.

However, efficiency cannot be maximized only by simply improving theorganic material layer. This is because long life span and highefficiency can be simultaneously achieved when energy levels and T1values among the respective layers included in the organic materiallayer, inherent material properties (mobility, interfacial properties,etc.) and the like are optimal combination.

In addition, an emission-auxiliary layer must be present between thehole transport layer and the light emitting layer in order to solve theproblem of luminescence in the hole transport layer of recent organicelectroluminescent devices, and material of different emission-auxiliarylayers have been developed for each of the light emitting layers (R, G,B).

In general, an electron is transferred from an electron transport layerto a light emitting layer and a hole is transferred from a holetransport layer to the light emitting layer, as a result, an exciton isformed by the recombination of the electron and hole. However, thematerial used for the hole transport layer has a low HOMO value andtherefore has a low T1 value. As a result, the exciton generated in thelight emitting layer is transferred to the hole transport layer,resulting in a charge unbalance in the light emitting layer and light isemitted at the interface of the hole transport layer.

When light is emitted at the interface of the hole transport layer, thecolor purity and efficiency of the organic electric element are loweredand a problem occurs in that the life time is shortened. Therefore, itis necessary to develop the emission-auxiliary layer material having ahigh T1 value and a HOMO level between the hole transport layer and thelight emitting layer.

Object, Technical Solution and Effects of the Invention

The object of the present invention is to provide a compound capable oflowering the driving voltage of an organic electronic element andimproving the luminous efficiency and life time, particularly the lifetime of the element, an organic electric element comprising thecompound, and an electronic device thereof.

In an aspect of the present invention, the present invention provides acompound represented by the following formula.

In another aspect of the present invention, the present inventionprovides an organic electric element employing the compound representedby the formula above and an electronic device thereof.

By using the compound according to one embodiment of the presentinvention, the driving voltage of an organic electric element can belowered and the luminous efficiency and lifetime of the element can beimproved, in particular, the lifetime can be largely improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1 to 3 each illustrate an embodiment of an organicelectroluminescent element according to the present invention: 100, 200,300 are an organic electric element, 110 is a first electrode, 120 is ahole injection layer, 130 is a hole transport layer, 140 is a lightemitting layer, 150 is an electron transport layer, 160 is an electroninjection layer, 170 is a second electrode, 180 is a light efficiencyimproving layer, 210 is a buffer layer, 220 is an emission-auxiliarylayer, 320 is a first hole injection layer, 330 is a first holetransport layer, 340 is a first light emitting layer, 350 is a firstelectron transport layer, 360 is a first charge generation layer, 361 isa second charge generation layer, 420 is a second hole injection layer,430 is a second hole transport layer, 440 is a second light emittinglayer, 450 is a second electron transport layer, CGL is a chargegeneration layer, ST1 is a first stack and ST2 is a second stack.

DETAILED DESCRIPTION

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. The arylgroup or arylene group in the present invention may comprise amonocyclic ring, ring assemblies, a fused polycyclic system, spirocompounds and the like. In addition, unless otherwise stated, afluorenyl group may be comprised in an aryl group and a fluorenylenegroup may be comprised in an arylene group.

Unless otherwise stated, the term “fluorenyl group”, “fluorenylenegroup” or “fluorenylenetriyl group” as used herein means univalent,bivalent or trivalent functional group in which R, R′ and R″ are allhydrogen in the following structure, “substituted fluorenyl group”,“substituted fluorenylene group” or “substituted fluorenylenetriylgroup” means that at least any one of R, R′ and R″ is a substituentother than hydrogen, and the case where R and R′ are bonded to eachother to form the spiro compound together with the carbon bonded to themis comprised. In this specification, a fluorene group, a fluorenylenegroup, and a fluorenyl group may be referred to as a fluorene groupregardless of the valence.

The term “spiro compound” as used herein has a spiro union which meansunion having one atom as the only common member of two rings. The commonatom is designated as ‘spiro atom’. The compounds are defined as‘monospiro-’, ‘dispiro-’ or ‘trispiro-’ depending on the number of spiroatoms in one compound.

The term “heterocyclic group” used in the specification comprises anon-aromatic ring as well as an aromatic ring like “heteroaryl group” or“heteroarylene group”. Unless otherwise stated, the term “heterocyclicgroup” means, but not limited to, a ring containing one or moreheteroatoms and having 2 to 60 carbon atoms. Unless otherwise stated,the term “heteroatom” as used herein represents N, O, S, P or Si and theheterocyclic group means a monocyclic, ring assemblies, fused polycyclicsystem or spiro compound containing a heteroatom. In addition,heterocyclic group comprises the compound comprising the heteroatomgroup such as SO₂, P═O etc. instead of carbon forming a ring such as thefollowing compound.

The term “aliphatic ring group” as used herein refers to a cyclichydrocarbon except for aromatic hydrocarbons, and comprises a monocyclicring, ring assemblies, a fused polycyclic system, spiro compounds, andthe like, and unless otherwise specified, it means a ring of 3 to 60carbon atoms, but not limited thereto. For example, a fused ring formedby benzene being an aromatic ring with cyclohexane being a non-aromaticring corresponds to aliphatic ring group.

In this specification, a‘group name’ corresponding to an aryl group, anarylene group, a heterocyclic group, and the like exemplified for eachsymbol and its substituent may be written in the name of functionalgroup reflecting the valence, and may also be described as the name of aparent compound. For example, in the case of phenanthrene which is akind of aryl group, it may be described by distinguishing valence suchas ‘phenanthryl (group)’ when it is ‘monovalent group’, and as‘phenanthrylene (group)’ when it is ‘divalent group’, and it may also bedescribed as a parent compound name, ‘phenanthrene’, regardless of itsvalence. Similarly, in the case of pyrimidine, it may be described as‘pyrimidine’ regardless of its valence, and it may also be described asthe name of corresponding functional group such as pyrimidinyl (group)when it is ‘monovalent group’, and as ‘pyrimidylene (group)’ when it is‘divalent group’.

In addition, in the present specification, the numbers and alphabetsindicating a position may be omitted when describing a compound name ora substituent name, For example, pyrido[4,3-d]pyrimidine,benzopuro[2,3-d] pyrimidine and 9,9-dimethyl-9H-fluorene can bedescribed as pyridopyrimidine, benzofurropyrimidine anddimethylfluorene, respectively. Therefore, both benzo[g]quinoxaline andbenzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless otherwise expressed, where any formula of thepresent invention is represented by the following formula, thesubstituent according to the index may be defined as follows.

In the above formula, where a is an integer of zero, the substituent R¹is absent, that is, hydrogen atoms are bonded to all the carbonconstituting the benzene ring. Here, chemical formulas or compounds maybe written without explicitly describing the hydrogen. In addition, onesubstituent R¹ is bonded to any carbon of the carbons forming thebenzene ring when “a” is an integer of 1. Similarly, where “a” is aninteger of 2 or 3, substituents R¹s may be bonded to the carbon of thebenzene ring, for example, as followings. Also, where “a” is an integerof 4 to 6, substituents R¹s are bonded to the carbon of the benzene ringin a similar manner. Further, where “a” is an integer of 2 or more, R¹smay be the same or different from each other.

In addition, unless otherwise specified in the present specification,when referring to a condensed/fused ring, the number in the‘number-condensed/fused ring’ indicates the number of condensed/fusedrings. For example, a condensed ring in which three rings arecondensed/fused with each other, such as anthracene, phenanthrene, andbenzoquinazoline, may be represented by a ‘3-condensed/fused ring.’

In addition, unless otherwise described herein, in the case ofexpressing a ring in the form of a ‘number-membered ring,’ such as a5-membered ring or a 6-membered ring, the number in the ‘number-memberedring’ represents the number of atoms forming the ring. For example,thiophene or furan may be referred to a 5-membered ring, and benzene orpyridine may be referred to a 6-membered ring.

In addition, unless otherwise specified in the present specification,the ring formed by bonding between adjacent groups may be selected fromthe group consisting of a C₆-C₆₀ aromatic ring group, a fluorenyl group,a C₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, and a C₃-C₆₀ aliphaticring.

Unless otherwise stated, the term “between adjacent groups”, forexample, in case of the following Formulas, comprises not only “betweenR₁ and R₂”, “between R₂ and R₃”, “between R₃ and R₄”, “between R₅ andR₆”, but also “between R₇ and R₈” sharing one carbon, and may comprise“between substituents” attached to the atom (carbon or nitrogen)consisting different rings, such as “between R₁ and R₇”, “between R₁ andR₈”, or “between R₄ and R₅” and the like. That is, where there aresubstituents bonded to adjacent elements constituting the same ring, thesubstituents may be correspond “adjacent groups”, and even if there areno adjacent substituents on the same ring, substituents attached to theneighboring ring may be referred to “adjacent groups”.

In the following Formula, when the substituents bonded to the samecarbon, such as R₇ and R₈, are linked to each other to form a ring, acompound containing a spiro-moiety may be formed.

In addition, in the present specification, the expression ‘neighboringgroups may be linked to each other to form a ring’ is used in the samesense as ‘neighboring groups are linked selectively to each other toform a ring’, and a case where at least one pair of neighboring groupsmay be bonded to each other to form a ring.

Hereinafter, referring to FIGS. 1 to 3, a lamination structure of anorganic electric element including the compound of the present inventionwill be described.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. In addition, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used for defining an essence, orderor sequence of a corresponding component but used merely to distinguishthe corresponding component from other component(s). It will beunderstood that the expression “one component is “connected,” “coupled”or “joined” to another component” comprises the case where a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components as well as the case where the first component maybe directly connected, coupled or joined to the second component.

In addition, it will be understood that when an element such as a layer,film, region or substrate is referred to as being “on” or “over” anotherelement, it can be directly on the other element or intervening elementsmay also be present. In contrast, when an element is referred to asbeing “directly on” another element, there are no intervening elementspresent.

The FIGS. 1 to 3 are laminated structures for showing an example of anorganic electric element according to an embodiment of the presentinvention, respectively.

Referring to the FIG. 1, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 110formed on a substrate (not shown), a second electrode 170, and anorganic material layer formed between the first electrode 110 and thesecond electrode 170.

The first electrode 110 may be an anode (positive electrode), and thesecond electrode 170 may be a cathode (negative electrode). In the caseof an inverted organic electric element, the first electrode may be acathode, and the second electrode may be an anode.

The organic material layer may be comprised a hole injection layer 120,a hole transport layer 130, a light emitting layer 140, an electrontransport layer 150, and an electron injection layer 160. Specifically,a hole injection layer 120, a hole transport layer 130, a light emittinglayer 140, an electron transport layer 150, and an electron injectionlayer 160 are formed on the first electrode 110 in sequence.

Preferably, a layer for improving the luminous efficiency 180 may beformed one side of sides of the first electrode 110 and the secondelectrode 170, wherein one side is not facing the organic materiallayer, as a result the luminous efficiency of an organic electricelement can be improved.

For example, the light efficiency improving layer 180 may be formed onthe second electrode 170, as a result, in the case of a top emissionorganic light emitting diode, the optical energy loss due to SurfacePlasmon Polaritons (SPPs) at the second electrode 170 may be reduced andin the case of a bottom emission organic light emitting diode, the lightefficiency improving layer 180 may serve as a buffer for the secondelectrode 170.

Meanwhile, a buffer layer 210 or an emission-auxiliary layer 220 may befurther formed between the hole transport layer 130 and the lightemitting layer 140, which will be described with reference to FIG. 2.

Referring to FIG. 2, the organic electric element 200 according toanother embodiment of the present invention may comprise a holeinjection layer 120, a hole transport layer 130, a buffer layer 210, anemission-auxiliary layer 220, a light emitting layer 140, the electrontransport layer 150, the electron injection layer 160, and a secondelectrode 170 formed on a first electrode 110 in sequence, and a lightefficiency improving layer 180 may be formed on the second electrode170.

Although not shown in FIG. 2, an electron transport auxiliary layer maybe further formed between the light emitting layer 140 and the electrontransport layer 150.

In addition, according to another embodiment of the present invention,the organic material layer may be a form consisting of a plurality ofstacks, wherein the stacks comprise a hole transport layer, a lightemitting layer, and an electron transport layer, respectively. This willbe described with reference to FIG. 3.

Referring to FIG. 3, two or more sets of stacks of the organic materiallayers ST1 and ST2 may be formed between the first electrode 110 and thesecond electrode 170 in the organic electric element 300 according toanother embodiment of the present invention, wherein the organicmaterial layers are consisted of multiple layers, respectively, and thecharge generation layer CGL may be formed between the stacks of theorganic material layer.

Specifically, the organic electric element according to the embodimentof the present invention may comprise the first electrode 110, the firststack ST1, the charge generation layer CGL, the second stack ST2, andthe second electrode 170 and the light efficiency improving layer 180.

The first stack ST1 is an organic layer formed on the first electrode110, and the first stack ST1 may comprise the first hole injection layer320, the first hole transport layer 330, the first light emitting layer340 and the first electron transport layer 350 and the second stack ST2may comprise a second hole injection layer 420, a second hole transportlayer 430, a second light emitting layer 440 and a second electrontransport layer 450. As such, the first stack and the second stack maybe the organic layers having the same or different stacked structures.

The charge generation layer CGL may be formed between the first stackST1 and the second stack ST2. The charge generation layer CGL maycomprise a first charge generation layer 360 and a second chargegeneration layer 361. The charge generating layer CGL is formed betweenthe first light emitting layer 340 and the second light emitting layer440 to increase the current efficiency generated in each light emittinglayer and to smoothly distribute charges.

The first light emitting layer 340 may comprise a light emittingmaterial comprising a blue host doped with a blue fluorescent dopant andthe second light emitting layer 440 may comprise a light emittingmaterial comprising a green host doped with a greenish yellow dopant anda red dopant together, but the material of the first light emittinglayer 340 and the second light emitting layer 440 according to anembodiment of the present invention is not limited thereto.

In FIG. 3, n may be an integer of 1 to 5 and the charge generation layerCGL and the third stack may be further stacked on the second stack ST2when n is 2.

When a plurality of light emitting layers are formed in a multi-layerstack structure as shown in FIG. 3, it is possible to manufacture anorganic electroluminescent element that emits not only white light butalso various colors, wherein the white light is emitted by the mixingeffect of light emitted from each light emitting layer.

The mixture of the compound represented by Formula 1 can be used asmaterial of a hole injection layer 120, 320, 420, a hole transport layer130, 330, 430, a buffer layer 210, an emission-auxiliary layer 220, anelectron transport layer 150, 350, 450, an electron injection layer 160,a light emitting layer 140, 340, 440, or a layer for improving luminousefficiency 180, preferably as material of an emission-auxiliary layer220 and/or a layer for improving luminous efficiency 180.

Even if the core is the same core, the band gap, the electricalcharacteristics, the interface characteristics and the like may bedifferent depending on which substituent is bonded at which position.Therefore, it is necessary to study the selection of the core and thecombination of the core and the sub-substituent bonded to the core. Inparticular, long life span and high efficiency can be simultaneouslyachieved when the optimal combination of energy levels and T₁ values,inherent material properties (mobility, interfacial properties, etc.),and the like among the respective layers of an organic material layer isachieved.

Therefore, energy level and T₁ value between the respective layers ofthe organic material layer, inherent material properties (mobility,interfacial properties, etc.) and the like can be optimized by using themixture of the compound represented by Formula 1 as anemission-auxiliary layer 220 and/or a layer for improving luminousefficiency 180, and thus it is possible to simultaneously improve thelifetime and efficiency of the organic electric element.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate to formthe anode 110, forming the organic material layer comprising the holeinjection layer 120, the hole transport layer 130, the light emittinglayer 140, the electron transport layer 150, and the electron injectionlayer 160 thereon, and then depositing a material, which can be used asthe cathode 170, thereon. Also, an emission-auxiliary layer 220 may beformed between a hole transport layer 130 and a light emitting layer140, and an electron transport auxiliary layer (not shown) may befurther formed between a light emitting layer 140 and an electrontransport layer 150 and, as described above, a stack structure may beformed.

Also, the organic material layer may be manufactured in such a mannerthat the fewer layers are formed using various polymer materials by asoluble process or solvent process, for example, spin coating, nozzleprinting, inkjet printing, slot coating, dip coating, roll-to-roll,doctor blading, screen printing, or thermal transfer, instead ofdeposition. Since the organic material layer according to the presentinvention may be formed in various ways, the scope of protection of thepresent invention is not limited by a method of forming the organicmaterial layer.

The organic electric element according to an embodiment of the presentinvention may be of a top emission type, a bottom emission type, or adual emission type depending on the material used.

In addition, the organic electric element according to an embodiment ofthe present invention may be selected from the group consisting of anorganic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor, an element for monochromaticillumination and an element for quantum dot display.

Another embodiment of the present invention provides an electronicdevice including a display device which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, the compound according to an aspect of the presentinvention will be described.

The compound according to an aspect of the present invention isrepresented by formula 1 below.

In Formula 1, each of symbols may be defined as follows:

x and y are each an integer of 0 to 2, preferably, an integer of 0 or 1,and x+y is an integer greater than or equal to 1. Where x and y are each2 or more, each of L²s, each of L³s, each of Ar³s, each of Ar⁴s, each ofAr⁵s, each of Ar⁶s is the same or different from each other.

Ar¹ to Ar⁶ are each independently selected from the group consisting ofa C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si, and P, a C₃-C₆₀aliphatic ring group, -L′-N(R_(a))(R_(b)), Formula A-1 and Formula A-2,and at least one of Ar¹ to Ar⁶ is Formula A-1 or Formula A-2,

X¹ is O or S and X² is N(R′), O or S.

Where at least one of Ar¹ to Ar⁶ is an aryl group, the aryl group may bepreferably a C₆-C₃₀, more preferably a C₆-C₁₈ aryl group, for example,phenyl, biphenyl, naphthyl, terphenyl and the like.

Where at least one of Ar¹ to Ar⁶ is a heterocyclic group except forFormula A-1 or Formula A-2, the heterocyclic group may be preferably aC₂-C₃₀, more preferably a C₂-C₁₆ heterocyclic group, for example,dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiopheneand the like.

Where at least one of Ar¹ to Ar⁶ is a fluorenyl group, the fluorenylgroup may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene,9,9′-spirofluorene and the like.

R¹ to R⁶ are each independently selected from the group consisting ofhydrogen, deuterium, halogen, cyano group, nitro group, a C₆-C₆₀ arylgroup, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ringgroup, a C₁-C₃₀ alkyl group, a C₂-C₃₀ alkenyl group, a C₂-C₃₀ alkynylgroup, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and-L′-N(R_(a))(R_(b)), and adjacent groups together may be bonded to eachother to form a ring.

Here, the term ‘neighboring groups’ means neighboring R¹s, neighboringR²s, neighboring R³s, neighboring R⁴s, neighboring R⁵s, neighboring R⁶s,neighboring R³ and R′, and/or neighboring R⁴ and R′.

The ring formed by neighboring R¹s, neighboring R²s, neighboring R³s,neighboring R⁴s, neighboring R⁵s or/and neighboring R⁶s is/are a C₆-C₆₀aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si and P, or a C₃-C₆₀aliphatic ring. For example, where the aromatic ring is formed bybonding between neighboring groups, the aromatic ring may be preferablya C₆-C₂₀ aromatic ring group, more preferably, a C₆-C₁₄ aromatic ringgroup, for example, benzene, naphthalene, phenanthrene or the like.

Where neighboring R³ and R′, and/or neighboring R⁴ and R′ are bonded toeach other to form a ring, a heterocyclic ring containing N may beformed. The heterocyclic ring may comprise a moiety, such as indole,carbazole, phenothiazine, phenoxazine, acridine, or the like.

n, p′ and r′ are each an integer of 0 to 3, m, o, p, q and r are each aninteger of 0 to 4, where they are each an integer of 2 or more, each ofR¹s, each of R²s, each of R³s, each of R⁴s, each of R⁵s, each of R⁶s isthe same or different from each other.

Where at least one of R¹ to R⁶ is an aryl group, the aryl group may bepreferably a C₆-C₃₀, more preferably a C₆-C₁ aryl group, for example,phenyl, biphenyl, naphthyl, terphenyl and the like.

Where at least one of R¹ to R⁶ is a heterocyclic group, the heterocyclicgroup may be preferably a C₂-C₃₀, more preferably a C₂-C₁₈ heterocyclicgroup, for example, dibenzothiophene, dibenzofuran, carbazole,phenylcarbazole and the like.

Where at least one of R¹ to R⁶ is an alkyl group, the alkyl group may bepreferably a C₁-C₁₀ alkyl group, for example, methyl, t-butyl and thelike.

Where at least one of R¹ to R⁶ is an alkoxyl group, the alkoxyl groupmay be preferably a C₁-C₂₀ alkoxy group, more preferably a C₁-C₁₀ alkoxygroup, for example, methoxy, t-butoxy and the like.

L¹ to L³ and L′ are each independently selected from the groupconsisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylenegroup, a C₃-C₆₀ aliphatic ring group and a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si, and P.

Where at least one of L¹ to L³ and L′ is an arylene group, the arylenegroup may be preferably a C₆-C₃₀, more preferably a C₆-C₁ arylene group,for example, phenylene, naphthalene, biphenyl, terphenyl and the like.

R′, R_(a) and R_(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P and a C₃-C₆₀ aliphatic ring group.

Where at least one of R′, R_(a) and R_(b) is an aryl group, the arylgroup may be preferably a C₆-C₃₀, more preferably a C₆-C₁ aryl group,for example, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene and thelike.

Where at least one of R′, R_(a) and R_(b) is a heterocyclic group, theheterocyclic group may be preferably a C₂-C₃₀, more preferably a C₂-C₁₈heterocyclic group, for example, carbazole, phenylcarbazole,dibenzofuran, dibenzothiophene and the like.

Where at least one of R′, R_(a) and R_(b) is a fluorenyl group, thefluorenyl group may be 9,9-dimethyl-9H-fluorene,9,9-diphenyl-9H-fluorene, 9,9′-spirofluorene and the like.

Ar¹ to Ar⁶, R¹ to R⁶, L¹ to L³, R′ and the ring formed by adjacentgroups may be each optionally substituted with one or more substituentsselected from the group consisting of deuterium, halogen, a silane groupunsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ arylgroup, a siloxane group, a boron group, a germanium group, a cyanogroup, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, aC₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio group, a C₁-C₂₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, afluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, aC₇-C₂₀ arylalkyl group, and C₈-C₂₀ arylalkenyl group.

Formula 1 may be represented by Formula 2 or Formula 3.

In Formulas 2 and 3, X¹, L¹-L³, Ar¹-Ar⁶, R¹, R², n, m are the same asdefined for Formula 1.

In addition, Formula 1 may be represented by one of Formula 4 to Formula19.

In Formulas 4 to 19, X¹, L¹-L³, Ar¹-Ar⁶, R¹, R², n, m are the same asdefined for Formula 1.

In addition, Formula 1 may be represented by one of Formula 20 toFormula 34.

In Formulas 20 to 34, X¹, L¹-L³, Ar¹-Ar⁶, R¹, R², n, mare the same asdefined for Formula 1, and a and b are each an integer of 0 to 6.

Specifically, the compound represented by formula 1 may be one of thefollowing compounds, but there is no limitation thereto.

In another aspect of the present invention, the present inventionprovides an organic electric element comprising an anode, a cathode, andan organic material layer formed between the anode and the cathode,wherein the organic material layer comprises a single compound or two ormore compounds represented by Formula 1.

In another aspect of the present invention, the present inventionprovides an organic electric element comprising an anode, a cathode, anorganic material layer formed between the anode and the cathode, and alayer for improving luminous efficiency. Here, the layer for improvingluminous efficiency is formed on one side of the anode or the cathode,the one side is not facing the organic material layer and the layer forimproving luminous efficiency comprises compound represented by Formula1.

The organic material layer comprises at least one of a hole injectionlayer, a hole transport layer, an emission-auxiliary layer, a lightemitting layer, an electron transport-auxiliary layer, an electrontransport layer and an electron injection layer, preferably, thecompound may be comprised in the emission-auxiliary layer.

The organic material layer may comprise two or more stacks, wherein thestacks may comprise a hole transport layer, a light emitting layer, andan electron transport layer formed in sequence on the anode, and acharge generation layer may be formed between the two or more stacks.

In another aspect of the present invention, the present inventionprovides an electronic device comprising a display device and a controlunit for controlling the display device, wherein the display devicecomprises the organic electric element comprising compound representedby Formula 1.

Hereinafter, synthesis example of the compound represented by Formula 1and preparation method of an organic electroluminescent elementaccording to the present invention will be described in detail by way ofexamples. However, the present invention is not limited to the followingexamples.

Synthesis Example

The compound (final product) represented by Formula 1 according to thepresent invention can be synthesized according to the reaction route ofthe following Reaction Scheme 1, but there is no limitation thereto.

I. Synthesis of Sub1

Sub 1 of the Reaction Scheme 1 can be synthesized according to thereaction route of the following Reaction Scheme 2-1 or 2-2, but there isno limitation thereto. Sub 1 can be synthesized according to thereaction route of the following Reaction Scheme 2-1 where X¹ is S andaccording to the reaction route of the following Reaction Scheme 2-2where X¹ is O.

1. Synthesis Example of Sub1-1, Sub1-7

(1) Synthesis Example of Sub1-1-a

(3-chlorophenyl)boronic acid (50.0 g, 320 mmol) was dissolved in THE(1.6 L), (2-bromo-6-iodophenyl)(ethyl)sulfane (110 g, 320 mmol), NaOH(38.4 g, 959 mmol), Pd(PPh₃)₄ (22.2 g, 19.2 mmol) and water (800 mL)were added thereto and the mixture was stirred at 80° C. When thereaction was completed, the reaction product was extracted with CH₂Cl₂and water, and then the organic layer was dried with MgSO₄ andconcentrated. Then, the concentrate was separated through a silica gelcolumn and recrystallized to obtain 88.0 g (yield: 84%) of the product.

(2) Synthesis Example of Sub1-1-b

Acetic acid (1.1 L) and 35% Hydrogen peroxide (H₂O₂) (76.7 mL) wereadded to Sub1-1-a (88.0 g, 269 mmol) and the mixture was stirred at roomtemperature. When the reaction was completed, the reaction product wasneutralized with an aqueous NaOH solution and extracted with EA(ethylacetate) and water. Thereafter, the organic layer was dried withMgSO₄ and concentrated. Then, the concentrate was separated through asilica gel column and recrystallized to obtain 82.2 g (yield: 89%) ofthe product.

(3) Synthesis Example of Sub1-1, Sub1-7

After adding Sub1-1-b (82.2 g, 239 mmol) to an excess oftrifluoromethane-sulfonic acid, the mixture was stirred at roomtemperature for 24 hours Thereafter, water and pyridine (8:1) wereslowly added thereto and the mixture was refluxed for 30 minutes. Thereaction product was cooled down and extracted with CH₂Cl₂ and water.Thereafter, the organic layer was dried with MgSO₄ and concentrated.Then, the concentrate was separated through a silica gel column andrecrystallized to obtain Sub1-1 28.5 g (yield: 40%) and Sub1-7 29.9 g(yield: 42%) of the products.

2. Synthesis Example of Sub1-13

(1) Synthesis Example of Sub1-13-a

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using (4-chlorophenyl) boronic acid (20.0 g, 128mmol), THF, (4-bromo-2-iodophenyl)(ethyl)sulfane (43.9 g, 128 mmol),NaOH (15.4 g, 384 mmol), Pd(PPh₃)₄ (8.87 g, 7.67 mmol) and water toobtain 33.9 g (yield: 81%) of product.

(2) Synthesis Example of Sub1-13-b

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-b using Sub1-13-a (33.9 g, 104 mmol), acetic acid (414mL) and 35% Hydrogen peroxide (H₂O₂) (29.6 mL) to obtain 32.8 g (yield:92%) of product.

(3) Synthesis Example of Sub1-13

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1 using Sub1-13-b (32.8 g, 95.3 mmol) instead of Sub1-1-bto obtain 23.8 g (yield: 84%) of the product.

3. Synthesis Example of Sub1-35

(1) Synthesis Example of Sub1-35-c

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using (4-chlorophenyl) boronic acid (20.0 g, 128mmol), 4-bromo-2-iodophenol (38.2 g, 128 mmol), NaOH (15.3 g, 384 mmol),Pd(PPh₃)₄ (8.87 g, 7.67 mmol) to obtain 29.7 g (yield: 82%) of product.

(2) Synthesis Example of Sub1-35

Pd(OAc)₂ (1.18 g, 5.24 mmol), 3-nitropyridine (0.65 g, 5.24 mmol),BzOOt-Bu (tert-butyl peroxybenzoate) (40.7 g, 210 mmol), C₆F₆(hexafluorobenzene) (160 mL), DMI (N,N′-dimethylimidazolidinone) (105mL) were added to Sub1-35-c (29.7 g, 105 mmol) and the mixture wasrefluxed at 90° C. for 3 hours. When the reaction was completed, thereaction product was cooled to room temperature, and extracted with EAand water. The organic layer was dried with MgSO₄ and concentrated.Thereafter, the concentrate was separated by a silica gel column andrecrystallized to obtain 19.2 g (yield: 65%) of the product.

4. Synthesis Example of Sub1-40

(1) Synthesis Example of Sub1-40-c

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using (2-chlorophenyl) boronic acid (20.0 g, 128mmol), 4-bromo-2-iodophenol (38.2 g, 128 mmol), NaOH (15.3 g, 384 mmol),Pd(PPh₃)₄ (8.87 g, 7.67 mmol) to obtain 29.0 g (yield: 80%) of product.

(2) Synthesis Example of Sub1-40

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using Sub1-40-c (29.0 g, 102 mmol), Pd(OAc)₂ (1.15 g,5.12 mmol), 3-nitropyridine (0.64 g, 5.12 mmol), BzOOt-Bu (tert-butylperoxybenzoate) (39.7 g, 205 mmol), C₆F₆ (hexafluorobenzene) (150 mL),DMI (N,N′-dimethylimidazolidinone) (100 mL) were added to Sub1-40-c(29.0 g, 102 mmol) to obtain 17.9 g (yield 62%) of product.

5. Synthesis Example of Sub1-46

(1) Synthesis Example of Sub1-46-a

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using (3-chloronaphthalen-2-yl) boronic acid (20.0 g,96.9 mmol), (5-bromo-2-iodophenyl)(ethyl)sulfane (33.2 g, 96.9 mmol),NaOH (11.6 g, 291 mmol), Pd(PPh₃)₄ (6.72 g, 5.81 mmol) to obtain 31.5 g(yield: 86%) of product.

(2) Synthesis Example of Sub1-46-b

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-b using Sub1-46-a (31.5 g, 83.3 mmol), acetic acid (333mL), 35% Hydrogen peroxide (H₂O₂) (23.8 mL) to obtain 28.5 g (yield:87%) of product.

(3) Synthesis Example of Sub1-46

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1 using Sub1-1-46-b (28.5 g, 72.5 mmol) to obtain 20.9 g(yield: 83%) of product.

6. Synthesis Example of Sub1-88

(1) Synthesis Example of Sub1-88-a

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using (1-chloronaphthalen-2-yl) boronic acid (20.0 g,96.9 mmol), (4′-bromo-4-iodo-[1,1′-biphenyl]-3-yl)(ethyl)sulfane (40.6g, 96.9 mmol), NaOH (11.6 g, 291 mmol), Pd(PPh₃)₄ (6.72 g, 5.81 mmol) toobtain 35.6 g (yield: 81%) of product.

(2) Synthesis Example of Sub1-88-b

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-b using Sub1-88-a (35.6 g, 78.5 mmol), acetic acid (314mL), 35% Hydrogen peroxide (H₂O₂) (22.4 mL) to obtain 34.3 g (yield:93%) of product.

(3) Synthesis Example of Sub1-88

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1 using Sub1-1-88-b (34.3 g, 73.0 mmol) instead ofSub1-1-b to obtain 23.8 g (yield: 77%) of the product.

7. Synthesis Example of Sub1-90

(1) Synthesis Example of Sub1-90-a

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using Phenylboronic acid (20.0 g, 164 mmol),5-bromo-3-iodo-2-(methylthio)phenol (56.6 g, 164 mmol), NaOH (19.7 g,492 mmol), Pd(PPh₃)₄ (11.4 g, 9.84 mmol) to obtain 41.2 g (yield: 85%)of product.

(2) Synthesis Example of Sub1-90-b

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-b using Sub1-90-a (41.2 g, 139 mmol), acetic acid (40mL), 35% Hydrogen peroxide (H₂O₂) (560 mL) to obtain 40.8 g (yield: 94%)of product.

(3) Synthesis Example of Sub1-90

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1 using Sub1-1-90-b (40.8 g, 131 mmol) to obtain 28.9 g(yield: 79%) of product.

8. Synthesis Example of Sub1-92

(1) Synthesis Example of Sub1-92-a

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using (5-bromo-2-chlorophenyl) boronic acid (30.0 g,128 mmol), (2-iodophenyl)(methyl)sulfane (31.9 g, 128 mmol), NaOH (15.3g, 383 mmol), Pd(PPh₃)₄ (8.84 g, 7.65 mmol) to obtain 32.8 g (yield:82%) of product.

(2) Synthesis Example of Sub1-92-b

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-b using Sub1-92-a (32.8 g, 105 mmol), acetic acid (30mL), 35% Hydrogen peroxide (H₂O₂) (420 mL) to obtain 33.1 g (yield: 96%)of product.

(3) Synthesis Example of Sub1-92

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1 using Sub1-1-92-b (33.1 g, 100 mmol) to obtain 21.5 g(yield: 72%) of product.

9. Synthesis Example of Sub1-96

(1) Synthesis Example of Sub1-96-a

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using (2-bromo-4-chlorophenyl) boronic acid (30.0 g,128 mmol), (2-iodophenyl)(methyl)sulfane (31.9 g, 128 mmol), NaOH (15.3g, 383 mmol), Pd(PPh₃)₄ (8.84 g, 7.65 mmol) to obtain 32.4 g (yield:81%) of product.

(2) Synthesis Example of Sub1-96-b

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-b using Sub1-96-a (32.4 g, 103 mmol), acetic acid (30mL), 35% Hydrogen peroxide (H₂O₂) (420 mL) to obtain 32.0 g (yield: 94%)of product.

(3) Synthesis Example of Sub1-96

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1 using Sub1-1-96-b (32.0 g, 97.1 mmol) to obtain 22.0 g(yield: 76%) of product.

10. Synthesis Example of Sub1-102

(1) Synthesis Example of Sub1-102-c

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using (2-chlorophenyl) boronic acid (20.0 g, 164mmol), 4-bromo-2-iodophenol (54.7 g, 164 mmol), NaOH (19.7 g, 492 mmol),Pd(PPh₃)₄ (11.4 g, 9.84 mmol) to obtain 40.0 g (yield: 86%) of product.

(2) Synthesis Example of Sub1-102

The reaction was carried out in the same manner as in the synthesismethod of Sub1-35 using Sub1-102-c (40.0 g, 141 mmol), Pd(OAc)₂ (1.58 g,7.05 mmol), 3-nitropyridine (0.88 g, 7.05 mmol), BzOOt-Bu (tert-butylperoxybenzoate) (54.8 g, 282 mmol), C₆F₆ (hexafluorobenzene) (210 mL),DMI (N,N′-dimethylimidazolidinone) (140 mL) to obtain 25.0 g (yield 63%)of product.

11. Synthesis Example of Sub1-106

(1) Synthesis Example of Sub1-106-c

The reaction was carried out in the same manner as in the synthesismethod of Sub1-1-a using Phenylboronic acid (20.0 g, 164 mmol),3-bromo-4-chloro-2-iodophenol (54.7 g, 164 mmol), NaOH (19.7 g, 492mmol), Pd(PPh₃)₄ (11.4 g, 9.84 mmol) to obtain 38.6 g (yield: 83%) ofproduct.

(2) Synthesis Example of Sub1-106

The reaction was carried out in the same manner as in the synthesismethod of Sub1-35 using Sub1-106-c (38.6 g, 136 mmol), Pd(OAc)₂ (1.53 g,6.81 mmol), 3-nitropyridine (0.85 g, 6.81 mmol), BzOOt-Bu (tert-butylperoxybenzoate) (52.9 g, 272 mmol), C₆F₆ (hexafluorobenzene) (200 mL),DMI (N,N′-dimethylimidazolidinone) (140 mL) to obtain 24.9 g (yield 65%)of product.

The compounds belonging to Sub 1 may be, but not limited to, thefollowing compounds, and Table 1 shows FD-MS (Field Desorption-MassSpectrometry) values of the following compounds.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 295.91(C₁₂H₆BrClS =297.59) Sub 1-2 m/z = 295.91(C₁₂H₆BrClS = 297.59) Sub 1-3 m/z =537.00(C₃₀H₁₇BrClNS = 538.89) Sub 1-4 m/z = 309.92(C₁₃H₈BrClS = 311.62)Sub 1-5 m/z = 313.90(C₁₂H₅BrClFS = 315.58) Sub 1-6 m/z =371.94(C₁₈H₁₀BrClS = 373.69) Sub 1-7 m/z = 295.91(C₁₂H₆BrClS = 297.59)Sub 1-8 m/z = 309.92(C₁₃H₈BrClS = 311.62) Sub 1-9 m/z =295.91(C₁₂H₆BrClS = 297.59) Sub 1-10 m/z = 461.95(C₂₄H₁₂BrClOS = 463.77)Sub 1-11 m/z = 295.91(C₁₂H₆BrClS = 297.59) Sub 1-12 m/z =309.92(C₁₃H₈BrClS = 311.62) Sub 1-13 m/z = 295.91(C₁₂H₆BrClS = 297.59)Sub 1-14 m/z = 309.92(C₁₃H₈BrClS = 311.62) Sub 1-15 m/z =295.91(C₁₂H₆BrClS = 297.59) Sub 1-16 m/z = 295.91(C₁₂H₆BrClS = 297.59)Sub 1-17 m/z = 295.91(C₁₂H₆BrClS = 297.59) Sub 1-18 m/z =295.91(C₁₂H₆BrClS = 297.59) Sub 1-19 m/z = 279.93(C₁₂H₆BrClO = 281.53)Sub 1-20 m/z = 355.96(C₁₈H₁₀BrClO = 357.63) Sub 1-21 m/z =304.92(C₁₃H₅BrClNO = 306.54) Sub 1-22 m/z = 309.94(C₁₃H₈BrClO₂ = 311.56)Sub 1-23 m/z = 297.92(C₁₂H₅BrClFO = 299.52) Sub 1-24 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub 1-25 m/z = 297.92(C₁₂H₅BrClFO = 299.52)Sub 1-26 m/z = 293.94(C₁₃H₈BrClO = 295.56) Sub 1-27 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub 1-28 m/z = 309.94(C₁₃H₈BrClO₂ = 311.56)Sub 1-29 m/z = 355.96(C₁₈H₁₀BrClO = 357.63) Sub 1-30 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub 1-31 m/z = 304.92(C₁₃H₅BrClNO = 306.54)Sub 1-32 m/z = 279.93(C₁₂H₆BrClO = 281.53) Sub 1-33 m/z =297.92(C₁₂H₅BrClFO = 299.52) Sub 1-34 m/z = 304.92(C₁₃H₅BrClNO = 306.54)Sub 1-35 m/z = 279.93(C₁₂H₆BrClO = 281.53) Sub 1-36 m/z =293.94(C₁₃H₈BrClO = 295.56) Sub 1-37 m/z = 279.93(C₁₂H₆BrClO = 281.53)Sub 1-38 m/z = 297.92(C₁₂H₅BrClFO = 299.52) Sub 1-39 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub 1-40 m/z = 279.93(C₁₂H₆BrClO = 281.53)Sub 1-41 m/z = 355.96(C₁₈H₁₀BrClO = 357.63) Sub 1-42 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub 1-43 m/z = 345.92(C₁₆H₈BrClS = 347.65)Sub 1-44 m/z = 329.94(C₁₆H₈BrClO = 331.59) Sub 1-45 m/z =329.94(C₁₆H₈BrClO = 331.59) Sub 1-46 m/z = 329.94(C₁₆H₈BrClO = 331.59)Sub 1-47 m/z = 345.92(C₁₆H₈BrClS = 347.65) Sub 1-48 m/z =345.92(C₁₆H₈BrClS = 347.65) Sub 1-49 m/z = 329.94(C₁₆H₈BrClO = 331.59)Sub 1-50 m/z = 329.94(C₁₆H₈BrClO = 331.59) Sub 1-51 m/z =345.92(C₁₆H₈BrClS = 347.65) Sub 1-52 m/z = 345.92(C₁₆H₈BrClS = 347.65)Sub 1-53 m/z = 329.94(C₁₆H₈BrClO = 331.59) Sub 1-54 m/z =329.94(C₁₆H₈BrClO = 331.59) Sub 1-55 m/z = 395.94(C₂₀H₁₀BrClS = 397.71)Sub 1-56 m/z = 395.94(C₂₀H₁₀BrClS = 397.71) Sub 1-57 m/z =379.96(C₂₀H₁₀BrClO = 381.65) Sub 1-58 m/z = 379.96(C₂₀H₁₀BrClO = 381.65)Sub 1-59 m/z = 395.94(C₂₀H₁₀BrClS = 397.71) Sub 1-60 m/z =395.94(C₂₀H₁₀BrClS = 397.71) Sub 1-61 m/z = 379.96(C₂₀H₁₀BrClO = 381.65)Sub 1-62 m/z = 379.96(C₂₀H₁₀BrClO = 381.65) Sub 1-63 m/z =395.94(C₂₀H₁₀BrClS = 397.71) Sub 1-64 m/z = 395.94(C₂₀H₁₀BrClS = 397.71)Sub 1-65 m/z = 379.96(C₂₀H₁₀BrClO = 381.65) Sub 1-66 m/z =379.96(C₂₀H₁₀BrClO = 381.65) Sub 1-67 m/z = 395.94(C₂₀H₁₀BrClS = 397.71)Sub 1-68 m/z = 395.94(C₂₀H₁₀BrClS = 397.71) Sub 1-69 m/z =379.96(C₂₀H₁₀BrClO = 381.65) Sub 1-70 m/z = 379.96(C₂₀H₁₀BrClO = 381.65)Sub 1-71 m/z = 395.94(C₂₀H₁₀BrClS = 397.71) Sub 1-72 m/z =395.94(C₂₀H₁₀BrClS = 397.71) Sub 1-73 m/z = 379.96(C₂₀H₁₀BrClO = 381.65)Sub 1-74 m/z = 379.96(C₂₀H₁₀BrClO = 381.65) Sub 1-75 m/z =395.94(C₂₀H₁₀BrClS = 397.71) Sub 1-76 m/z = 395.94(C₂₀H₁₀BrClS = 397.71)Sub 1-77 m/z = 379.96(C₂₀H₁₀BrClO = 381.65) Sub 1-78 m/z =379.96(C₂₀H₁₀BrClO = 381.65) Sub 1-79 m/z = 371.94(C₁₈H₁₀BrClS = 373.69)Sub 1-80 m/z = 405.98(C₂₂H₁₂BrClO = 407.69) Sub 1-81 m/z =355.96(C₁₈H₁₀BrClO = 357.63) Sub 1-82 m/z = 371.94(C₁₈H₁₀BrClS = 373.69)Sub 1-83 m/z = 421.95(C₂₂H₁₂BrClS = 423.75) Sub 1-84 m/z =477.93(C₂₄H₁₂BrClS₂ = 479.83) Sub 1-85 m/z = 355.96(C₁₈H₁₀BrClO =357.63) Sub 1-86 m/z = 371.99(C₁₉H₁₄BrClO = 373.67) Sub 1-87 m/z =421.95(C₂₂H₁₂BrClS = 423.75) Sub 1-88 m/z = 421.95(C₂₂H₁₂BrClS = 423.75)Sub 1-89 m/z = 310.00(C₁₄H₁₅BrOS = 311.24) Sub 1-90 m/z =310.00(C₁₄H₁₅BrOS = 311.24) Sub 1-91 m/z = 492.02(C₂₆H₂₁ BrOS₂ = 493.48)Sub 1-92 m/z = 327.97(C₁₄H₁₄BrClS = 329.68) Sub 1-93 m/z =341.98(C₁₅H₁₆BrClS = 343.71) Sub 1-94 m/z = 386.03(C₂₀H₁₉BrOS = 387.34)Sub 1-95 m/z = 293.97(C₁₃H₁₁BrOS = 295.19) Sub 1-96 m/z =311.94(C₁₃H₁₀BrClS = 313.64) Sub 1-97 m/z = 336.93(C₁₄H₉BrClNS = 338.65)Sub 1-98 m/z = 327.97(C₁₄H₁₄BrClS = 329.68) Sub 1-99 m/z =311.99(C₁₄H₁₄BrClO = 313.62) Sub 1-100 m/z = 342.00(C₁₅H₁₆BrClO₂ =343.65) Sub 1-101 m/z = 311.99(C₁₄H₁₄BrClO = 313.62) Sub 1-102 m/z =311.99(C₁₄H₁₄BrClO = 313.62) Sub 1-103 m/z = 295.96(C₁₃H₁₀BrClO =297.58) Sub 1-104 m/z = 313.95(C₁₃H₉BrClFO = 315.57) Sub 1-105 m/z =295.96(C₁₃H₁₀BrClO = 297.58) Sub 1-106 m/z = 311.99(C₁₄H₁₄BrClO =313.62) Sub 1-107 m/z = 343.96(C₁₄H₁₄BrClOS = 345.68) Sub 1-108 m/z =311.96(C₁₃H₁₀BrClO₂ = 313.58) Sub 1-109 m/z = 360.02(C₁₈H₁₇BrOS =361.30) Sub 1-110 m/z = 362.01(C₁₈H₁₆BrClO = 363.68) Sub 1-111 m/z =345.98(C₁₇H₁₂BrClO = 347.64) Sub 1-112 m/z = 361.95(C₁₇H₁₂BrClS =363.70) Sub 1-113 m/z = 361.95(C₁₇H₁₂BrClS = 363.70) Sub 1-114 m/z =362.01(C₁₈H₁₆BrClO = 363.68)

II. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 can be synthesized by the reaction route ofthe following Reaction Scheme 3, as disclosed in Korean PatentRegistration No. 10-1251451, published on Apr. 5, 2013 and filed by thepresent applicant, but it is not limited thereto. In the followingReaction Scheme 3, Z¹ is Ar¹, Ar³ or Ar⁵, Z² is Ar², Ar⁴ or Ar⁶, andHal⁴ is Br or Cl.

Where Z¹ is represented by Formula A-1 or Formula A-2, Z¹—Hal⁴ ofReaction Scheme 3 may be synthesized by the reaction route of thefollowing Reaction Scheme 4, but there is no limitation thereto. X², R³to R⁶, o to r are the same as defined for Formula A-1 or Formula A-2, Xis —OH, —SH, —NH₂, one of R⁴ and R⁶ is Hal⁴, and Hal is Br or Cl.

The reaction proceeds according to the synthetic route of (1) where X′is —OH, the synthetic route of (2) where X′ is —SH, and the syntheticroute of (3) where X′ is —NH₂.

1. Synthesis Example of Sub2-29

(1) Synthesis Example of Sub 2-29-b

After putting 2-iodobenzoic acid (50.0 g, 202 mmol), thiophenol (22.2 g,202 mmol), Potassium hydroxide (56.6 g, 1008 mmol), Copper powder (1.3g, 20.2 mmol) in around bottom flask, water (1.3 L) was added theretoand the mixture was refluxed for 12 hours. When the reaction iscompleted, the reaction product was cooled to room temperature, and 3MHCl was added until precipitation was complete. Thereafter, theprecipitate was washed with water and dried to obtain 41.3 g (yield 89%)of the product.

(2) Synthesis Example of Sub 2-29-c

After adding H₂SO₄ (1.3 mL) to the starting material Sub 2-29-b (41.3 g,179 mmol), the mixture was refluxed until the starting material wasdissolved. When the starting material was dissolved, the solution wascooled to room temperature and then ice water was added to precipitate.After that, the precipitate was washed with water, dried and dissolvedin CH₂C₂. Then, the resultant was separated through a silica gel columnand recrystallized to obtain 25.9 g (yield 68%) of the product.

(3) Synthesis Example of Sub 2-29-d

2-bromo-4′-chloro-1,1′-biphenyl (32.6 g, 122 mmol) was dissolved in THE(270 mL) under a nitrogen atmosphere, and then cooled to −78° C. Thenn-BuLi (49 mL) was slowly added thereto and the mixture was stirred for30 minutes. Subsequently, after Sub 2-29-c (25.9 g, 122 mmol) wasdissolved in THE (140 mL), the solution was slowly added dropwise to themixture. After stirring at −78° C. for one hour, the temperature wasgradually raised to room temperature. When the reaction is completed,the resultant was extracted with ethyl acetate and water, and theorganic layer is dried with MgSO₄ and concentrated. Thereafter, theconcentrate was separated by a silica gel column and recrystallized toobtain 40.1 g (yield 82%) of the product.

(4) Synthesis Example of Sub 2-29-e

Sub 2-29-d (40.1 g, 100 mmol), acetic acid (250 mL) and concentratedhydrochloric acid (40 mL) were placed in a round bottom flask andstirred under nitrogen atmosphere at 60-80° C. for 3 hours. When thereaction was completed, the reaction product was extracted with CH₂Cl₂and water, and the organic layer is dried with MgSO₄ and concentrated.Thereafter, the concentrate was separated by a silica gel column andrecrystallized to obtain 31.8 g (yield 83%) of the product.

(5) Synthesis Example of Sub 2-29

After dissolving Sub 2-29-e (31.8 g, 83.0 mmol) in toluene (420 mL),aniline (7.7 g, 83.0 mmol), Pd₂(dba)₃ (2.28 g, 2.49 mmol), P(t-Bu)₃(1.01 g, 4.98 mmol) and NaOt-Bu (16.0 g, 166 mmol)) were added andstirred at 90° C. When the reaction was completed, the reaction productwas extracted with CH₂Cl₂ and water, and the organic layer is dried withMgSO₄ and concentrated. Thereafter, the concentrate was separated by asilica gel column and recrystallized to obtain 28.5 g (yield 78%) of theproduct.

2. Synthesis Example of Sub 2-39

(1) Synthesis Example of Sub 2-39-b

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-b using 3-chloro-2-iodobenzoic acid (20.0 g, 70.8mmol), 3-(dibenzo[b,d]furan-3-yl)benzenethiol (19.6 g, 70.8 mmol), KOH(19.9 g, 354 mmol), Copper powder (0.45 g, 7.08 mmol) to obtain 25.6 g(yield 84%).

(2) Synthesis Example of Sub 2-39-c

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-c using Sub 2-39-b (25.6 g, 59.4 mmol), H₂SO₄ (420mL) to obtain 14.7 g (yield 60%).

(3) Synthesis Example of Sub 2-39-d

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-d using 2-bromo-1,1′-biphenyl (8.3 g, 35.6 mmol),n-BuLi (14 mL), Sub 2-39-c (14.7 g, 35.6 mmol) to obtain 16.4 g (yield81%).

(4) Synthesis Example of Sub 2-39-e

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-e using Sub 2-39-d (16.4 g, 28.8 mmol), acetic acid(72 mL) and concentrated hydrochloric acid (12 mL) to obtain 12.0 g(yield 76%).

(5) Synthesis Example of Sub 2-39

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29 using Sub 2-39-e (12.0 g, 21.9 mmol), aniline (2.0 g,21.9 mmol), Pd₂(dba)₃ (0.60 g, 0.66 mmol), P(t-Bu)₃ (0.27 g, 1.31 mmol),NaOt-Bu (4.2 g, 43.7 mmol) to obtain 9.4 g (yield 71%).

3. Synthesis Example of Sub 2-46

(1) Synthesis Example of Sub 2-46-b

After putting 2-iodobenzoic acid (50.0 g, 202 mmol), Phenol (37.9 g, 403mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (90.4 g, 605 mmol),pyridine (3.2 mL), copper powder (1.7 g, 26.2 mmol) and CuI (1.7 g, 9.07mmol) in a round flask, DMF (1.6 L) was added thereto and the mixturewas refluxed for 3 hours. When the reaction was completed, the reactionproduct was cooled to room temperature, and 3M HCl was added untilprecipitation was complete. Thereafter, the precipitate was washed withwater and dried to obtain 41.8 g (yield 86%) of the product.

(2) Synthesis Example of Sub 2-46-c

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-c using Sub 2-46-b (41.8 g, 195 mmol), H₂SO₄ (14 L)to obtain 26.4 g (yield 69%) of product.

(3) Synthesis Example of Sub 2-46-d

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-d using 2-bromo-2′-chloro-1,1′-biphenyl (36.0 g, 135mmol), n-BuLi (54 mL), Sub 2-46-c (26.4 g, 135 mmol) to obtain 45.1 g(yield 87%) of product.

(4) Synthesis Example of Sub 2-46-e

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-e using Sub 2-46-d (45.1 g, 117 mmol), acetic acid(290 mL) and concentrated hydrochloric acid (50 mL) to obtain 40.4 g(yield 94%) of product.

(5) Synthesis Example of Sub 2-46

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29 using Sub 2-46-e (40.4 g, 110 mmol), aniline (10.3 g,110 mmol), Pd₂(dba)₃ (3.03 g, 3.30 mmol), P(t-Bu)₃ (1.34 g, 6.61 mmol),NaOt-Bu (21.2 g, 220 mmol) to obtain 35.0 g (yield 75%) of product.

4. Synthesis Example of Sub 2-47

(1) Synthesis Example of Sub 2-47-b

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-46-b using 5-chloro-2-iodobenzoic acid (50.0 g, 177mmol), Phenol (33.3 g, 354 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) (79.4 g, 531 mmol), pyridine (2.9 mL), copper powder (1.5 g, 23.0mmol), CuI (1.5 g, 7.97 mmol) to obtain 38.3 g (yield 87%) of product.

(2) Synthesis Example of Sub 2-47-c

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-c using Sub 2-47-b (38.3 g, 154 mmol), H₂SO₄ (1.1 L)to obtain 23.1 g (yield 65%) of product.

(3) Synthesis Example of Sub 2-47-d

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-d using 2-bromo-1,1′-biphenyl (23.3 g, 100 mmol),n-BuLi (40 mL), Sub 2-47-c (23.1 g, 100 mmol) to obtain 32.8 g (yield85%) of product.

(4) Synthesis Example of Sub 2-47-e

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-e using Sub 2-47-d (32.8 g, 85.1 mmol), acetic acid(210 mL) and concentrated hydrochloric acid (35 mL) to obtain 28.4 g(yield 91%) of product.

(5) Synthesis Example of Sub 2-47

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29 using Sub 2-47-e (28.4 g, 77.4 mmol), aniline (7.2 g,77.4 mmol), Pd₂(dba)₃ (2.13 g, 2.32 mmol), P(t-Bu)₃ (0.94 g, 4.65 mmol),NaOt-Bu (14.9 g, 155 mmol) to obtain 23.9 g (yield 73%) of product.

5. Synthesis Example of Sub 2-75

(1) Synthesis Example of Sub 2-75-a

After putting 2-iodobenzoic acid (20.0 g, 80.6 mmol), 4-chloroaniline(20.6 g, 161 mmol), Cu(OAc)₂ (1.0 g), Sodium acetate (7.9 g, 96.8 mmol)in a round flask, water (540 mL) was added thereto and the mixture wasrefluxed for 5 hours. When the reaction was completed, the reactionproduct was cooled to room temperature, and 3M HCl was added untilprecipitation was complete. Thereafter, the precipitate was washed withwater and dried to obtain 16.4 g (yield 82%) of the product.

(2) Synthesis Example of Sub 2-75-b

After dissolving Sub 2-75-a (16.4 g, 66.2 mmol) in toluene (330 mL),1-bromonaphthalene (13.7 g, 66.2 mmol), Pd₂(dba)₃ (1.82 g, 1.99 mmol),P(t-Bu)₃ (0.80 g, 3.97 mmol) and NaOt-Bu (12.7 g, 132 mmol) were addedthe solution and the mixture was stirred at 60° C. When the reaction wascompleted, the reaction product was extracted with CH₂C₂ and water, andthe organic layer was dried with MgSO₄ and concentrated. Thereafter, theconcentrate was separated by a silica gel column and recrystallized toobtain 18.3 g (yield 74%) of the product.

(3) Synthesis Example of Sub 2-75-c

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-c using Sub 2-75-b (18.3 g, 49.0 mmol), H₂SO₄ (350mL) to obtain 11.8 g (yield 68%) of product.

(4) Synthesis Example of Sub 2-75-d

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-d using 2-bromo-2′-chloro-1,1′-biphenyl (7.7 g, 33.2mmol), n-BuLi (13 mL), Sub 2-75-c (11.8 g, 33.2 mmol) to obtain 13.9 g(yield 82%) of product.

(5) Synthesis Example of Sub 2-75-e

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-e using Sub 2-75-d (13.9 g, 27.2 mmol), acetic acid(68 mL) and concentrated hydrochloric acid (11 mL) to obtain 12.3 g(yield 92%) of product.

(6) Synthesis Example of Sub 2-75

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29 using Sub 2-75-e (12.3 g, 25.0 mmol), aniline (2.3 g,25.0 mmol), Pd₂(dba)₃ (0.69 g, 0.75 mmol), P(t-Bu)₃ (0.30 g, 1.50 mmol),NaOt-Bu (4.8 g, 50.0 mmol) to obtain 10.7 g (yield 78%) of product.

6. Synthesis Example of Sub 2-81

(1) Synthesis Example of Sub 2-81-f

2-bromo-N-(4-chlorophenyl)-N-phenylnaphthalen-1-amine (20.0 g, 48.9mmol) was dissolved in THE (100 mL) under a nitrogen atmosphere, andthen cooled to −78° C. Then n-BuLi (20 mL) was slowly added thereto andthe mixture was stirred for 30 minutes. Subsequently, after9H-fluoren-9-one (8.8 g, 48.9 mmol) was dissolved in THE (60 mL), thesolution was slowly added dropwise to the mixture. After stirring at−78° C. for one hour, the temperature was gradually raised to roomtemperature. When the reaction is completed, the resultant was extractedwith ethyl acetate and water, and the organic layer is dried with MgSO₄and concentrated. Thereafter, the concentrate was separated by a silicagel column and recrystallized to obtain 21.2 g (yield 85%) of theproduct.

(2) Synthesis Example of Sub 2-81-e

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-e using Sub 2-81-f (21.2 g, 41.6 mmol), acetic acid(100 mL) and concentrated hydrochloric acid (20 mL) to obtain 9.8 g(yield 48%) of product.

(3) Synthesis Example of Sub 2-81

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29 using Sub 2-81-e (9.8 g, 19.9 mmol),[1,1′-biphenyl]-4-amine (3.4 g, 19.9 mmol), Pd₂(dba)₃ (0.55 g, 0.60mmol), P(t-Bu)₃ (0.24 g, 1.20 mmol), NaOt-Bu (3.8 g, 39.8 mmol) toobtain 9.5 g (yield 76%) of product.

7. Synthesis Example of Sub 2-83

(1) Synthesis Example of Sub 2-83-f

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-81-f using 9-(2-bromo-4-chlorophenyl)-9H-carbazole (20.0g, 56.1 mmol), n-BuLi (22 mL), 9H-fluoren-9-one (10.1 g, 56.1 mmol) toobtain 22.3 g (yield 81%) of product.

(2) Synthesis Example of Sub 2-83-e

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29-e using Sub 2-83-f (22.3 g, 45.4 mmol), acetic acid(110 mL) and concentrated hydrochloric acid (20 mL) to obtain 17.8 g(yield 89%) of product.

(3) Synthesis Example of Sub 2-83

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-29 using Sub 2-83-e (17.8 g, 40.5 mmol), aniline (3.8 g,40.5 mmol), Pd₂(dba)₃ (1.11 g, 1.21 mmol), P(t-Bu)₃ (0.49 g, 2.43 mmol),NaOt-Bu (7.8 g, 80.9 mmol) to obtain 14.3 g (yield 71%) of product.

The compounds belonging to Sub 2 may be, but not limited to, thefollowing compounds, and Table 2 shows FD-MS (Field Desorption-MassSpectrometry) values of the following compounds.

TABLE 2 OwOHHd FD-MS Compound FD-MS Sub 2-1 m/z = 169.09(C

H

N = 169.23) Sub 2-2 m/z = 245.12(C

H

N = 245.33) Sub 2-3 m/z = 245.12(C

H

N = 245.33) Sub 2-4 m/z = 321.15(C

H

N = 321.42) Sub 2-5 m/2 = 321.15(C

H

N = 321.42) Sub 2-6 m/z = 321.15(C

H

N = 321.42) Sub 2-7 m/z = 219.10(C

H

N = = 219.29) Sub 2-8 m/z = 219.10(C

H

N = 219.29) Sub 2-9 m/z = 269.12(C

H

N = 269.35) Sub 2-10 m/z = 269.12(C

H

N = 269.35) Sub 2-11 m/z = 421.18(C

H

N = 421.54) Sub 2-12 m/z = 421.18(C

H

N = 421.54) Sub 2-13 m/z = 179.15(C

HD

N = 179.29) Sub 2-14 m/z = 281.21(C

H

N = 281.44) Sub 2-15 m/z = 281.21(C

H

N = 281.44) Sub 2-16 m/z = 241.15(C

H

NO = 241.33) Sub 2-17 m/z = 313.20(C

H

NO₂ = 313.44) Sub 2-18 m/z = 194.08(C

H

N₂ = 194.24) Sub 2-19 m/z = 187.08(C

H

FN = 187.22) Sub 2-20 m/z = 205.07(C

H

F₂N = 205.21) Sub 2-21 m/z = 285.15(C

H

N = 285.39) Sub 2-22 m/z = 407.17(C

H

N = 407.52) Sub 2-23 m/z = 275.08(C

H

NS = 275.37) Sub 2-24 m/z = 259.10(C

H

NO = 259.31) Sub 2-25 m/z = 259.10(C

H

NO = 259.31) Sub 2-26 m/z = 325.09(C

H

NS = 325.43) Sub 2-27 m/z = 309.12(C

H

NO = 309.37) Sub 2-28 m/z = 309.12(C

H

NO = 309.37) Sub 2-29 m/z = 439.14(C

H

NS = 439.58) Sub 2-30 m/z = 439.14(C

H

NS = 439.58) Sub 2-31 m/z = 439.14(C

H

NS = 439.58) Sub 2-32 m/z = 439.14(C

H

NS = 439.58) Sub 2-33 m/z = 439.14(C

H

NS = 439.58) Sub 2-34 m/z = 439.14(C

H

NS = 439.58) Sub 2-35 m/z = 515.17(C

H

NS = 515.67) Sub 2-36 m/z = 489.16(C

H

NS = 489.64) Sub 2-37 m/z = 515.17(C

H

NS = 515.67) Sub 2-38 m/z = 515.17(C

H

NS = 515.67) Sub 2-39 m/z = 605.18(C

H

NOS = 605.76) Sub 2-40 m/z = 489.16(C

H

NS = 489.64) Sub 2-41 m/z = 489.16(C

H

NS = 489.64) Sub 2-42 m/z = 489.16(C

H

NS = 489.64) Sub 2-43 m/z = 489.16(C

H

NS = 489.64) Sub 2-44 m/z = 423.16(C

H

NO = 423.52) Sub 2-45 m/z = 423.16(C

H

NO = 423.52) Sub 2-46 m/z = 423.16(C

H

NO = 423.52) Sub 2-47 m/z = 423.16(C

H

NO = 423.52) Sub 2-48 m/z = 423.16(C

H

NO = 423.52) Sub 2-49 m/z = 423.16(C

H

NO = 423.52) Sub 2-50 m/z = 423.16(C

H

NO = 423.52) Sub 2-51 m/z = 441.15(C

H

FNO = 441.51) Sub 2-52 m/z = 499.19(C

H

NO = 499.61) Sub 2-53 m/z = 499.19(C

H

NO = 499.61) Sub 2-54 m/z = 473.18(C

H

NO = 473.58) Sub 2-55 m/z = 473.18(C

H

NO = 473.58) Sub 2-56 m/z = 529.15(C

H

NOS = 529.66) Sub 2-57 m/z = 473.18(C

H

NO = 473.58) Sub 2-58 m/z = 473.18(C

H

NO = 473.58) Sub 2-59 m/z = 473.18(C

H

NO = 473.58) Sub 2-60 m/z = 473.18(C

H

NO = 473.58) Sub 2-61 m/z = 473.18(C

H

NO = 473.58) Sub 2-62 m/z = 473.18(C

H

NO = 473.58) Sub 2-63 m/z = 473.18(C

H

NO = 473.58) Sub 2-64 m/z = 473.18(C

H

NO = 473.58) Sub 2-65 m/z = 498.21(C

H

N₂ = 498.63) Sub 2-66 m/z = 498.21(C

H

N₂ = 498.63) Sub 2-67 m/z = 498.21(C

H

N₂ = 498.63) Sub 2-68 m/z = 498.21(C

H

N₂ = 498.63) Sub 2-69 m/z = 498.21(C₃₇H₂₆N₂ = 498.63) Sub 2-70 m/z =498.21(C₃₇H₂₆N₂ = 498.63) Sub 2-71 m/z = 574.24(C₄₃H₃₀N₂ = 574.73) Sub2-72 m/z = 574.24(C₄₃H₃₀N₂ = 574.73) Sub 2-73 m/z = 574.24(C₄₃H₃₀N₂ =574.73) Sub 2-74 m/z = 548.23(C₄₁H₂₈N₂ = 548.69) Sub 2-75 m/z =548.23(C₄₁H₂₈N₂ = 548.69) Sub 2-76 m/z = 548.23(C₄₁H₂₈N₂ = 548.69) Sub2-77 m/z = 598.24(C₄₅H₃₀N₂ = 598.75) Sub 2-78 m/z = 604.20(C₄₃H₂₈N₂S =604.77) Sub 2-79 m/z = 663.27(C₄₉H₃₃N₃ = 663.82) Sub 2-80 m/z =614.27(C₄₆H₃₄N₂ = 614.79) Sub 2-81 m/z = 624.26(C₄₇H₃₂N₂ = 624.79) Sub2-82 m/z = 496.19(C₃₇H₂₄N₂ = 496.61) Sub 2-83 m/z = 496.19(C₃₇H₂₄N₂ =496.61) Sub 2-84 m/z = 496.19(C₃₇H₂₄N₂ = 496.61) Sub 2-85 m/z =546.21(C₄₁H₂₆N₂ = 546.67) Sub 2-86 m/z = 528.17(C₃₇H₂₄N₂S = 528.67) Sub2-87 m/z = 528.17(C₃₇H₂₄N₂S = 528.67) Sub 2-88 m/z = 528.17(C₃₇H₂₄N₂S =528.67) Sub 2-89 m/z = 512.19(C₃₇H₂₄N₂O = 512.61) Sub 2-90 m/z =587.24(C₄₃H₂₉N₃ = 587.73) Sub 2-91 m/z = 538.24(C₄₀H₃₀N₂ = 538.69)

indicates data missing or illegible when filed

III. Synthesis Example of Final Product 1. Synthesis Example of P-1

(1) Synthesis Example of Inter-1

After dissolving Sub1-1 (2.00 g, 6.72 mmol) in toluene (35 mL), Sub 2-1(1.14 g, 6.72 mmol), Pd₂(dba)₃ (0.18 g, 0.20 mmol), P(t-Bu)₃ (0.08 g,0.40 mmol) and NaOt-Bu (1.29 g, 13.4 mmol) were added and stirred at 60°C. When the reaction was completed, the reaction product was extractedwith CH₂Cl₂ and water, and the organic layer is dried with MgSO₄ andconcentrated. Thereafter, the concentrate was separated by a silica gelcolumn and recrystallized to obtain 1.95 g (yield 75%) of the product.

(2) Synthesis Example of P-1

After Inter-1 (1.95 g, 5.04 mmol) was dissolved in toluene (25 mL), Sub2-29 (2.22 g, 5.04 mmol), Pd₂(dba)₃ (0.14 g, 0.15 mmol), P(t-Bu)₃ (0.06g, 0.30 mmol) and NaOt-Bu (0.97 g, 10.1 mmol) were added thereto and themixture was refluxed. When the reaction was completed, the reactionproduct was extracted with CH₂Cl₂ and water, and the organic layer isdried with MgSO₄ and concentrated. Thereafter, the concentrate wasseparated by a silica gel column and recrystallized to obtain 2.86 g(yield 72%) of the product.

2. Synthesis Example of P-45

(1) Synthesis Example of Inter-45

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-13 (2.00 g, 6.72 mmol), Sub 2-1 (1.14 g,6.72 mmol), Pd₂(dba)₃ (0.18 g, 0.20 mmol), P(t-Bu)₃ (0.08 g, 0.40 mmol),NaOt-Bu (1.29 g, 13.4 mmol) to obtain 1.87 g (yield 72%) of product.

(2) Synthesis Example of P-45

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-45 (1.87 g, 4.84 mmol), Sub 2-29 (2.05 g, 4.84mmol), Pd₂(dba)₃ (0.13 g, 0.15 mmol), P(t-Bu)₃ (0.06 g, 0.29 mmol),NaOt-Bu (0.93 g, 9.68 mmol) to obtain 2.62 g (yield 70%) of product.

3. Synthesis Example of P-50

(1) Synthesis Example of Inter-50

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-15 (2.00 g, 6.72 mmol), Sub 2-1 (1.14 g,6.72 mmol), Pd₂(dba)₃ (0.18 g, 0.20 mmol), P(t-Bu)₃ (0.08 g, 0.40 mmol),NaOt-Bu (1.29 g, 13.4 mmol) to obtain 1.82 g (yield 70%) of product.

(2) Synthesis Example of P-50

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-50 (1.82 g, 4.70 mmol), Sub 2-44 (1.99 g, 4.70mmol), Pd₂(dba)₃ (0.13 g, 0.14 mmol), P(t-Bu)₃ (0.06 g, 0.28 mmol),NaOt-Bu (0.90 g, 9.41 mmol) to obtain 2.84 g (yield 78%) of product.

4. Synthesis Example of P-64

(1) Synthesis Example of Inter-64

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-16 (2.00 g, 6.72 mmol), Sub 2-1 (1.14 g,6.72 mmol), Pd₂(dba)₃ (0.18 g, 0.20 mmol), P(t-Bu)₃ (0.08 g, 0.40 mmol),NaOt-Bu (1.29 g, 13.4 mmol) to obtain 2.00 g (yield 77%) of product.

(2) Synthesis Example of P-64

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-64 (2.00 g, 5.17 mmol), Sub 2-83 (2.57 g, 5.17mmol), Pd₂(dba)₃ (0.14 g, 0.16 mmol), P(t-Bu)₃ (0.06 g, 0.31 mmol),NaOt-Bu (0.99 g, 10.4 mmol) to obtain 3.15 g (yield 72%) of product.

5. Synthesis Example of P-83

(1) Synthesis Example of Inter-83

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-23 (2.00 g, 6.68 mmol), Sub 2-4 (2.15 g,6.68 mmol), Pd₂(dba)₃ (0.18 g, 0.20 mmol), P(t-Bu)₃ (0.08 g, 0.40 mmol),NaOt-Bu (1.28 g, 13.4 mmol) to obtain 2.63 g (yield 73%) of product.

(2) Synthesis Example of P-83

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-83 (2.63 g, 4.87 mmol), Sub 2-75 (2.67 g, 4.87mmol), Pd₂(dba)₃ (0.13 g, 0.15 mmol), P(t-Bu)₃ (0.06 g, 0.29 mmol),NaOt-Bu (0.94 g, 9.75 mmol) to obtain 3.49 g (yield 68%) of product.

6. Synthesis Example of P-112

After Sub1-32 (2.00 g, 7.10 mmol) was dissolved in toluene (40 mL), Sub2-45 (6.02 g, 14.21 mmol), Pd₂(dba)₃ (0.20 g, 0.21 mmol), P(t-Bu)₃ (0.09g, 0.43 mmol) and NaOt-Bu (1.37 g, 14.2 mmol) were added thereto and themixture was refluxed. When the reaction was completed, the reactionproduct was extracted with CH₂Cl₂ and water, and the organic layer isdried with MgSO₄ and concentrated. Thereafter, the concentrate wasseparated by a silica gel column and recrystallized to obtain 5.53 g(yield 77%) of the product.

7. Synthesis Example of P-117

(1) Synthesis Example of Inter-117

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-35 (2.00 g, 7.10 mmol), Sub 2-1 (1.20 g,7.10 mmol), Pd₂(dba)₃ (0.20 g, 0.21 mmol), P(t-Bu)₃ (0.09 g, 0.43 mmol),NaOt-Bu (1.37 g, 14.2 mmol) to obtain 2.00 g (yield 76%) of product.

(2) Synthesis Example of P-117

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-117 (2.00 g, 5.40 mmol), Sub 2-29 (2.37 g,5.40 mmol), Pd₂(dba)₃ (0.15 g, 0.16 mmol), P(t-Bu)₃ (0.07 g, 0.32 mmol),NaOt-Bu (1.04 g, 10.8 mmol) to obtain 3.09 g (yield 74%) of product.

8. Synthesis Example of P-132

(1) Synthesis Example of Inter-132

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-37 (2.00 g, 7.10 mmol), Sub 2-42 (3.36 g,7.10 mmol), Pd₂(dba)₃ (0.20 g, 0.21 mmol), P(t-Bu)₃ (0.09 g, 0.43 mmol),NaOt-Bu (1.37 g, 14.2 mmol) to obtain 3.40 g (yield 71%) of product.

(2) Synthesis Example of P-132

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-132 (3.40 g, 5.04 mmol), Sub 2-1 (0.85 g, 5.04mmol), Pd₂(dba)₃ (0.14 g, 0.15 mmol), P(t-Bu)₃ (0.06 g, 0.30 mmol),NaOt-Bu (0.97 g, 10.1 mmol) to obtain 3.22 g (yield 79%) of product.

9. Synthesis Example of P-136

(1) Synthesis Example of Inter-136

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-39 (2.00 g, 7.10 mmol), Sub2-87 (3.76 g,7.10 mmol), Pd₂(dba)₃ (0.20 g, 0.21 mmol), P(t-Bu)₃ (0.09 g, 0.43 mmol),NaOt-Bu (1.37 g, 14.2 mmol) to obtain 3.89 g (yield 75%) of product.

(2) Synthesis Example of P-136

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-136 (3.89 g, 5.33 mmol), Sub 2-13 (0.96 g,5.33 mmol), Pd₂(dba)₃ (0.15 g, 0.16 mmol), P(t-Bu)₃ (0.06 g, 0.32 mmol),NaOt-Bu (1.02 g, 10.7 mmol) to obtain 3.62 g (yield 78%) of product.

10. Synthesis Example of P-145

(1) Synthesis Example of Inter-145

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-40 (2.00 g, 7.10 mmol), Sub 2-33 (3.12 g,7.10 mmol), Pd₂(dba)₃ (0.20 g, 0.21 mmol), P(t-Bu)₃ (0.09 g, 0.43 mmol),NaOt-Bu (1.37 g, 14.2 mmol) to obtain 3.55 g (yield 78%) of product.

(2) Synthesis Example of P-145

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-145 (3.55 g, 5.54 mmol), Sub 2-1 (0.94 g, 5.54mmol), Pd₂(dba)₃ (0.15 g, 0.17 mmol), P(t-Bu)₃ (0.07 g, 0.33 mmol),NaOt-Bu (1.07 g, 11.1 mmol) to obtain 2.87 g (yield 67%) of product.

11. Synthesis Example of P-162

(1) Synthesis Example of Inter-162

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-52 (2.00 g, 5.75 mmol), Sub 2-1 (0.97 g,5.75 mmol), Pd₂(dba)₃ (0.16 g, 0.17 mmol), P(t-Bu)₃ (0.07 g, 0.35 mmol),NaOt-Bu (1.11 g, 11.5 mmol) to obtain 1.83 g (yield 73%) of product.

(2) Synthesis Example of P-162

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-162 (1.83 g, 4.20 mmol), Sub 2-45 (1.78 g,4.20 mmol), Pd₂(dba)₃ (0.12 g, 0.13 mmol), P(t-Bu)₃ (0.05 g, 0.25 mmol),NaOt-Bu (0.81 g, 8.40 mmol) to obtain 2.63 g (yield 76%) of product.

12. Synthesis Example of P-175

(1) Synthesis Example of Inter-175

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-65 (2.00 g, 5.24 mmol), Sub 2-1 (0.89 g,5.24 mmol), Pd₂(dba)₃ (0.14 g, 0.16 mmol), P(t-Bu)₃ (0.06 g, 0.31 mmol),NaOt-Bu (1.01 g, 10.5 mmol) to obtain 1.77 g (yield 72%) of product.

(2) Synthesis Example of P-175

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-175 (1.77 g, 3.77 mmol), Sub 2-83 (1.87 g,3.77 mmol), Pd₂(dba)₃ (0.10 g, 0.11 mmol), P(t-Bu)₃ (0.05 g, 0.23 mmol),NaOt-Bu (0.73 g, 7.55 mmol) to obtain 2.49 g (yield 71%) of product.

13. Synthesis Example of P-195

(1) Synthesis Example of Inter-195

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-85 (2.00 g, 5.59 mmol), Sub 2-44 (2.37 g,5.59 mmol), Pd₂(dba)₃ (0.15 g, 0.17 mmol), P(t-Bu)₃ (0.07 g, 0.34 mmol),NaOt-Bu (1.07 g, 11.2 mmol) to obtain 3.17 g (yield 81%) of product.

(2) Synthesis Example of P-195

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-195 (3.17 g, 4.53 mmol), Sub 2-1 (0.77 g, 4.53mmol), Pd₂(dba)₃ (0.12 g, 0.14 mmol), P(t-Bu)₃ (0.05 g, 0.27 mmol),NaOt-Bu (0.87 g, 9.06 mmol) to obtain 2.45 g (yield 65%) of product.

14. Synthesis Example of P-204

(1) Synthesis Example of Inter-204-a

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-90 (2.00 g, 7.16 mmol), Sub 2-5 (2.30 g,7.16 mmol), Pd₂(dba)₃ (0.20 g, 0.21 mmol), P(t-Bu)₃ (0.09 g, 0.43 mmol),NaOt-Bu (1.38 g, 14.3 mmol) to obtain 3.05 g (yield 82%) of product.

(2) Synthesis Example of Inter-204-b

After adding an excess of trifluoromethane-sulfonic acid to Inter-204-a(3.05 g, 5.87 mmol), the solution was stirred for 24 hours at roomtemperature. Water and pyridine (8:1) were slowly added the solution andthe mixture was refluxed for 30 minutes. After lowering the temperature,the resultant was extracted with CH₂Cl₂ and water. The organic layer wasdried with MgSO₄ and concentrated. Thereafter, the concentrate wasseparated by a silica gel column and recrystallized to obtain 1.89 g(yield: 73%) of the product.

(3) Synthesis Example of P-204

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-204-b (1.89 g, 4.29 mmol), Sub 2-33 (2.80 g,4.29 mmol), Pd₂(dba)₃ (0.12 g, 0.13 mmol), P(t-Bu)₃ (0.05 g, 0.26 mmol),NaOt-Bu (0.82 g, 8.58 mmol) to obtain 2.91 g (yield 72%) of product.

15. Synthesis Example of P-208

(1) Synthesis Example of Inter-208

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-92 (2.00 g, 6.72 mmol), Sub 2-1 (1.14 g,6.72 mmol), Pd₂(dba)₃ (0.18 g, 0.20 mmol), P(t-Bu)₃ (0.08 g, 0.40 mmol),NaOt-Bu (1.29 g, 13.4 mmol) to obtain 1.84 g (yield 71%) of product.

(2) Synthesis Example of P-208

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-208 (1.84 g, 4.77 mmol), Sub 2-32 (2.10 g,4.77 mmol), Pd₂(dba)₃ (0.13 g, 0.14 mmol), P(t-Bu)₃ (0.06 g, 0.29 mmol),NaOt-Bu (0.92 g, 9.54 mmol) to obtain 3.09 g (yield 82%) of product.

16. Synthesis Example of P-216

(1) Synthesis Example of Inter-216

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-96 (2.00 g, 6.72 mmol), Sub 2-47 (2.85 g,6.72 mmol), Pd₂(dba)₃ (0.18 g, 0.20 mmol), P(t-Bu)₃ (0.08 g, 0.40 mmol),NaOt-Bu (1.29 g, 13.4 mmol) to obtain 3.36 g (yield 78%) of product.

(2) Synthesis Example of P-216

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-216 (3.36 g, 5.24 mmol), Sub 2-1 (0.89 g, 5.24mmol), Pd₂(dba)₃ (0.14 g, 0.16 mmol), P(t-Bu)₃ (0.06 g, 0.31 mmol),NaOt-Bu (1.01 g, 10.5 mmol) to obtain 3.08 g (yield 76%) of product.

17. Synthesis Example of P-243

(1) Synthesis Example of Inter-243

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-106 (2.00 g, 7.10 mmol), Sub 2-1 (1.20 g,7.10 mmol), Pd₂(dba)₃ (0.20 g, 0.21 mmol), P(t-Bu)₃ (0.09 g, 0.43 mmol),NaOt-Bu (1.37 g, 14.2 mmol) to obtain 1.92 g (yield 73%) of product.

(2) Synthesis Example of P-243

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-243 (1.92 g, 5.19 mmol), Sub 2-34 (2.28 g,5.19 mmol), Pd₂(dba)₃ (0.14 g, 0.16 mmol), P(t-Bu)₃ (0.06 g, 0.31 mmol),NaOt-Bu (1.00 g, 10.4 mmol) to obtain 1.72 g (yield 43%) of product.

18. Synthesis Example of P-250

(1) Synthesis Example of Inter-250-a

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Sub1-102 (2.00 g, 7.10 mmol), Sub 2-1 (1.20 g,7.10 mmol), Pd₂(dba)₃ (0.20 g, 0.21 mmol), P(t-Bu)₃ (0.09 g, 0.43 mmol),NaOt-Bu (1.37 g, 14.2 mmol) to obtain 2.02 g (yield 77%) of product.

(2) Synthesis Example of Inter-250-b

After dissolving Inter-250-a (2.02 g, 5.47 mmol) in THE (27 mL),(4-hydroxyphenyl) boronic acid (0.75 g, 5.47 mmol), NaOH (0.66 g, 16.4mmol), Pd(PPh₃)₄ (0.38 g, 0.33 mmol) and water (14 mL) were added andthe mixture was stirred at 80° C. When the reaction was completed, thereaction product was extracted with CH₂Cl₂ and water, and the organiclayer is dried with MgSO₄ and concentrated. Thereafter, the concentratewas separated by a silica gel column and recrystallized to obtain 1.92 g(yield: 82%) of the product.

(3) Synthesis Example of Inter-250-c

The reaction was carried out in the same manner as in the synthesismethod of Inter-204-b using Inter-250-b (1.92 g, 4.49 mmol) to obtain1.83 g (yield: 73%) of product.

(4) Synthesis Example of P-250

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-250-c (1.83 g, 3.27 mmol), Sub 2-47 (1.39 g,3.27 mmol), Pd₂(dba)₃ (0.09 g, 0.10 mmol), P(t-Bu)₃ (0.04 g, 0.20 mmol),NaOt-Bu (0.63 g, 6.55 mmol) to obtain 2.05 g (yield 75%) of product.

19. Synthesis Example of P-254

(1) Synthesis Example of Inter-254-a

The reaction was carried out in the same manner as in the synthesismethod of Inter-250-b using Sub1-96 (2.0 g, 6.72 mmol),(4-hydroxyphenyl) boronic acid (0.93 g, 6.72 mmol), NaOH (0.81 g, 20.2mmol), Pd(PPh₃)₄ (0.47 g, 0.40 mmol) to obtain 1.75 g (yield: 84%) ofproduct.

(2) Synthesis Example of Inter-254-b

The reaction was carried out in the same manner as in the synthesismethod of Inter-1 using Inter-254-a (1.75 g, 5.65 mmol), Sub 2-47 (2.39g, 5.65 mmol), Pd₂(dba)₃ (0.16 g, 0.17 mmol), P(t-Bu)₃ (0.07 g, 0.34mmol), NaOt-Bu (1.09 g, 11.3 mmol) to obtain 2.84 g (yield 72%) ofproduct.

(3) Synthesis Example of Inter-254-c

The reaction was carried out in the same manner as in the synthesismethod of Inter-204-b using Inter-254-b (2.84 g, 4.06 mmol) to obtain2.56 g (yield: 76%) of product.

(4) Synthesis Example of P-254

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Inter-254-c (2.56 g, 3.09 mmol), Sub 2-1 (0.52 g,3.09 mmol), Pd₂(dba)₃ (0.08 g, 0.09 mmol), P(t-Bu)₃ (0.04 g, 0.19 mmol),NaOt-Bu (0.59 g, 6.18 mmol) to obtain 1.89 g (yield 72%) of product.

The FD-MS values of the compounds P-1 to P-266 of the present inventionprepared according to the above synthesis examples are shown in Table 3below.

TABLE 3 Compound FD-MS Compound FD-MS P-1 m/z = 788.23(C₅₅H₃₆N₂S₂ =789.03) P-2 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-3 m/z =860.29(C₅₉H₄₄N₂OS₂ = 861.13) P-4 m/z = 897.32(C₆₅H₄₃N₃S = 898.14) P-5m/z = 822.27(C₅₉H₃₈N₂OS = 823.03) P-6 m/z = 923.33(C₆₇H₄₅N₃S = 924.18)P-7 m/z = 845.29(C₆₁H₃₉N₃S = 846.06) P-8 m/z = 838.25(C₅₉H₃₈N₂S₂ =839.09) P-9 m/z = 877.26(C₆₁H₃₉N₃S₂ = 878.12) P-10 m/z =1119.33(C₇₉H₄₉N₃OS₂ = 1120.4) P-11 m/z = 782.32(C₅₅H₂₆D₁₀N₂OS = 783.03)P-12 m/z = 963.36(C₇₀H₄₉N₃S = 964.24) P-13 m/z = 836.29(C₆₀H₄₀N₂OS =837.05) P-14 m/z = 990.26(C₆₇H₄₀F₂N₂OS₂ = 991.19) P-15 m/z =879.27(C₆₁H₃₈FN₃OS = 880.05) P-16 m/z = 998.34(C₇₂H₄₆N₄S = 999.25) P-17m/z = 1016.33(C₇₃H₄₈N₂S₂ = 1017.32) P-18 m/z = 782.32(C₅₅H₂₆D₁₀N₂OS =783.03) P-19 m/z = 974.33(C₇₁H₄₆N₂OS = 975.22) P-20 m/z =1012.36(C₇₃H₄₈N₄S = 1013.28) P-21 m/z = 864.26(C₆₁H₄₀N₂S₂ = 865.13) P-22m/z = 973.35(C₇₁H₄₇N₃S = 974.24) P-23 m/z = 886.30(C₆₄H₄₂N₂OS = 887.11)P-24 m/z = 916.37(C₆₃H₅₂N₂O₃S = 917.18) P-25 m/z = 957.41(C₆₉H₅₅N₃S =958.28) P-26 m/z = 894.22(C₆₁H₃₈N₂S₃ = 895.17) P-27 m/z =1115.43(C₈₂H₅₇N₃S = 1116.44) P-28 m/z = 872.29(C₆₃H₄₀N₂OS = 873.09) P-29m/z = 788.23(C₅₅H₃₆N₂S₂ = 789.03) P-30 m/z = 942.31(C₆₇H₄₃FN₂OS =943.15) P-31 m/z = 847.30(C₆₁H₄₁N₃S = 848.08) P-32 m/z =1053.38(C₇₆H₅₁N₃OS = 1054.32) P-33 m/z = 940.29(C₆₇H₄₄N₂S₂ = 941.22)P-34 m/z = 786.27(C₅₆H₃₈N₂OS = 786.99) P-35 m/z = 847.30(C₆₁H₄₁N₃S =848.08) P-36 m/z = 838.25(C₅₉H₃₈N₂S₂ = 839.09) P-37 m/z =940.29(C₆₇H₄₄N₂S₂ = 941.22) P-38 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03) P-39m/z = 847.30(C₆₁H₄₁N₃S = 848.08) P-40 m/z = 786.27(C₅₆H₃₈N₂OS = 786.99)P-41 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97) P-42 m/z = 788.23(C₅₅H₃₆N₂S₂ =789.03) P-43 m/z = 861.32(C₆₂H₄₃N₃S = 862.11) P-44 m/z =772.25(C₅₅H₃₆N₂OS = 772.97) P-45 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97) P-46m/z = 788.23(C₅₅H₃₆N₂S₂ = 789.03) P-47 m/z = 847.30(C₆₁H₄₁N₃S = 848.08)P-48 m/z = 802.25(C₅₆H₃₈N₂S₂ = 803.05) P-49 m/z = 788.23(C₅₅H₃₆N₂S₂ =789.03) P-50 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97) P-51 m/z =847.30(C₆₁H₄₁N₃S = 848.08) P-52 m/z = 788.23(C₅₅H₃₆N₂S₂ = 789.03) P-53m/z = 940.29(C₆₇H₄₄N₂S₂ = 941.22) P-54 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03)P-55 m/z = 897.32(C₆₅H₄₃N₃S = 898.14) P-56 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-57 m/z = 824.21(C₅₅H₃₄F₂N₂S₂ = 825.01) P-58 m/z =924.32(C₆₇H₄₄N₂OS = 925.16) P-59 m/z = 959.43(C₆₉H₅₇N₃S = 960.30) P-60m/z = 877.26(C₆₁H₃₉N₃S₂ = 878.12) P-61 m/z = 888.26(C₆₃H₄₀N₂S₂ = 889.15)P-62 m/z = 947.33(C₆₉H₄₅N₃S = 948.20) P-63 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-64 m/z = 845.29(C₆₁H₃₉N₃S = 846.06) P-65 m/z =772.25(C₅₅H₃₆N₂OS = 772.97) P-66 m/z = 904.29(C₆₄H₄₄N₂S₂ = 905.19) P-67m/z = 1099.40(C₈₁H₅₃N₃S = 1100.40) P-68 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-69 m/z = 928.26(C₆₅H₄₀N₂OS₂ = 929.17) P-70 m/z =772.25(C₅₅H₃₆N₂OS = 772.97) P-71 m/z = 947.33(C₆₉H₄₅N₃S = 948.20) P-72m/z = 788.23(C₅₅H₃₆N₂S₂ = 789.03) P-73 m/z = 788.23(C₅₅H₃₆N₂S₂ = 789.03)P-74 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97) P-75 m/z = 1003.31(C₇₁H₄₅N₃S₂ =1004.28) P-76 m/z = 900.36(C₆₃H₅₂N₂S₂ = 901.24) P-77 m/z =848.29(C₆₁H₄₀N₂OS = 849.06) P-78 m/z = 920.35(C₆₇H₄₄N₄O = 921.12) P-79m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-80 m/z = 921.30(C₆₆H₃₉N₃O₃ = 922.06)P-81 m/z = 786.29(C₅₆H₃₈N₂O₃ = 786.93) P-82 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-83 m/z = 1051.39(C₇₇H₅₀FN₃O = 1052.27) P-84 m/z =931.36(C₆₉H₄₅N₃O = 932.14) P-85 m/z = 806.29(C₅₉H₃₈N₂O₂ = 806.97) P-86m/z = 782.32(C₅₅H₂₆D₁₀N₂OS = 783.03) P-87 m/z = 931.36(C₆₉H₄₅N₃O =932.14) P-88 m/z = 862.27(C₆₁H₃₈N₂O₂S = 863.05) P-89 m/z =924.32(C₆₇H₄₄N₂OS = 925.16) P-90 m/z = 824.28(C₅₉H₃₇FN₂O₂ = 824.96) P-91m/z = 908.34(C₆₇H₄₄N₂0₂ = 909.10) P-92 m/z = 845.34(C₆₂H₄₃N₃O = 846.05)P-93 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-94 m/z = 861.34(C₆₂H₄₃N₃O₂ =862.05) P-95 m/z = 797.25(C₅₆H₃₅N₃OS = 797.98) P-96 m/z =774.27(C₅₅H₃₅FN₂O₂ = 774.90) P-97 m/z = 924.32(C₆₇H₄₄N₂OS = 925.16) P-98m/z = 879.32(C₆₅H₄₁N₃O = 880.06) P-99 m/z = 832.31(C₆₁H₄₀N₂O₂ = 833.00)P-100 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-101 m/z = 808.24(C₅₅H₃₄F₂N₂OS= 808.95) P-102 m/z = 766.34(C₅₅H₂₆D₁₀N₂O₂ = 766.97) P-103 m/z =1083.42(C₈₁H₅₃N₃O = 1084.34) P-104 m/z = 797.25(C₅₆H₃₅N₃OS = 797.98)P-105 m/z = 856.31(C₆₃H₄₀N₂O₂ = 857.03) P-106 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-107 m/z = 983.39(C₇₃H₄₉N₃O = 984.22) P-108 m/z =1010.33(C₇₄H₄₈N₂OS = 1011.26) P-109 m/z = 884.38(C₆₃H₅₂N₂OS = 885.18)P-110 m/z = 925.35(C₆₇H₄₄FN₃O = 926.11) P-111 m/z = 856.31(C₆₃H₄₀N₂O₂ =857.03) P-112 m/z = 1010.35(C₇₄H₄₆N₂0₃ = 1011.19) P-113 m/z =867.31(C₆₁H₃₉F₂N₃O = 868.00) P-114 m/z = 781.27(C₅₆H₃₅N₃O₂ = 781.92)P-115 m/z = 1126.36(C₈₂H₅₀N₂O₂S = 1127.37) P-116 m/z =912.28(C₆₅H₄₀N₂O₂S = 913.11) P-117 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97)P-118 m/z = 907.36(C₆₇H₄₅N₃O = 908.12) P-119 m/z = 756.28(C₅₅H₃₆N₂O₂ =756.91) P-120 m/z = 786.27(C₅₆H₃₈N₂OS = 786.99) P-121 m/z =756.28(C₅₅H₃₆N₂O₂ = 756.91) P-122 m/z = 786.27(C₅₆H₃₈N₂OS = 786.99)P-123 m/z = 943.34(C₆₇H₄₃F₂N₃O = 944.10) P-124 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-125 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97) P-126 m/z =822.27(C₅₉H₃₈N₂OS = 823.03) P-127 m/z = 983.39(C₇₃H₄₉N₃O = 984.22) P-128m/z = 806.29(C₅₉H₃₈N₂O₂ = 806.97) P-129 m/z = 790.25(C₅₅H₃₅FN₂OS =790.96) P-130 m/z = 908.34(C₆₇H₄₄N₂O₂ = 909.10) P-131 m/z =931.36(C₆₉H₄₅N₃O = 932.14) P-132 m/z = 806.29(C₅₉H₃₈N₂O₂ = 806.97) P-133m/z = 806.29(C₅₉H₃₈N₂O₂ = 806.97) P-134 m/z = 884.38(C₆₃H₅₂N₂OS =885.18) P-135 m/z = 831.32(C₆₁H₄₁N₃O = 832.02) P-136 m/z =871.34(C₆₁H₂₉D₁₀N₃OS = 872.12) P-137 m/z = 808.24(C₅₅H₃₄F₂N₂OS = 808.95)P-138 m/z = 808.24(C₅₅H₃₄F₂N₂OS = 808.95) P-139 m/z = 957.37(C₇₁H₄₇N₃O =958.18) P-140 m/z = 832.31(C₆₁H₄₀N₂O₂ = 833.00) P-141 m/z =772.25(C₅₅H₃₆N₂OS = 772.97) P-142 m/z = 806.29(C₅₉H₃₈N₂O₂ = 806.97)P-143 m/z = 867.31(C₆₁H₃₉F₂N₃O = 868.00) P-144 m/z = 981.37(C₇₃H₄₇N₃O =982.20) P-145 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-146 m/z =756.28(C₅₅H₃₆N₂O₂ = 756.91) P-147 m/z = 1000.35(C₇₃H₄₈N₂OS = 1001.26)P-148 m/z = 831.32(C₆₁H₄₁N₃O = 832.02) P-149 m/z = 756.28(C₅₅H₃₆N₂O₂ =756.91) P-150 m/z = 756.28(C₅₅H₃₆N₂O₂ = 756.91) P-151 m/z =831.32(C₆₁H₄₁N₃O = 832.02) P-152 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97) P-153m/z = 838.25(C₅₉H₃₈N₂S₂ = 839.09) P-154 m/z = 806.29(C₅₉H₃₈N₂O₂ =806.97) P-155 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03) P-156 m/z =897.32(C₆₅H₄₃N₃S = 898.14) P-157 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03) P-158m/z = 838.25(C₅₉H₃₈N₂S₂ = 839.09) P-159 m/z = 987.33(C₇₁H₄₅N₃OS =988.22) P-160 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03) P-161 m/z =838.25(C₅₉H₃₈N₂S₂ = 839.09) P-162 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03)P-163 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03) P-164 m/z = 881.34(C₆₅H₄₃N₃O =882.08) P-165 m/z = 888.26(C₆₃H₄₀N₂S₂ = 889.15) P-166 m/z =947.33(C₆₉H₄₅N₃S = 948.20) P-167 m/z = 856.31(C₆₃H₄₀N₂O₂ = 857.03) P-168m/z = 872.29(C₆₃H₄₀N₂OS = 873.09) P-169 m/z = 872.29(C₆₃H₄₀N₂OS =873.09) P-170 m/z = 947.33(C₆₉H₄₅N₃S = 948.20) P-171 m/z =872.29(C₆₃H₄₀N₂OS = 873.09) P-172 m/z = 872.29(C₆₃H₄₀N₂OS = 873.09)P-173 m/z = 872.29(C₆₃H₄₀N₂OS = 873.09) P-174 m/z = 872.29(C₆₃H₄₀N₂OS =873.09) P-175 m/z = 929.34(C₆₉H₄₃N₃O = 930.12) P-176 m/z =872.29(C₆₃H₄₀N₂OS = 873.09) P-177 m/z = 888.26(C₆₃H₄₀N₂S₂ = 889.15)P-178 m/z = 872.29(C₆₃H₄₀N₂OS = 873.09) P-179 m/z = 931.36(C₆₉H₄₅N₃O =932.14) P-180 m/z = 872.29(C₆₃H₄₀N₂OS = 873.09) P-181 m/z =872.29(C₆₃H₄₀N₂OS = 873.09) P-182 m/z = 977.29(C₆₉H₄₃N₃S₂ = 978.24)P-183 m/z = 931.36(C₆₉H₄₅N₃O = 932.14) P-184 m/z = 856.31(C₆₃H₄₀N₂O₂ =857.03) P-185 m/z = 872.29(C₆₃H₄₀N₂OS = 873.09) P-186 m/z =947.33(C₆₉H₄₅N₃S = 948.20) P-187 m/z = 856.31(C₆₃H₄₀N₂O₂ = 857.03) P-188m/z = 872.29(C₆₃H₄₀N₂OS = 873.09) P-189 m/z = 848.29(C₆₁H₄₀N₂OS =849.06) P-190 m/z = 898.30(C₆₅H₄₂N₂OS = 899.12) P-191 m/z =907.36(C₆₇H₄₅N₃O = 908.12) P-192 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-193m/z = 914.28(C₆₅H₄₂N₂S₂ = 915.19) P-194 m/z = 1029.32(C₇₃H₄₇N₃S₂ =1030.32) P-195 m/z = 832.31(C₆₁H₄₀N₂O₂ = 833.00) P-196 m/z =864.32(C₆₂H₄₄N₂OS = 865.11) P-197 m/z = 898.3(C₆₅H₄₂N₂OS = 899.12) P-198m/z = 914.28(C₆₅H₄₂N₂S₂ = 915.19) P-199 m/z = 788.23(C₅₅H₃₆N₂S₂ =789.03) P-200 m/z = 847.30(C₆₁H₄₁N₃S = 848.08) P-201 m/z =772.25(C₅₅H₃₆N₂OS = 772.97) P-202 m/z = 954.27(C₆₇H₄₂N₂OS₂ = 955.21)P-203 m/z = 887.32(C₆₁H₂₉D₁₀N₃S₂ = 888.19) P-204 m/z = 940.29(C₆₇H₄₄N₂S₂= 941.22) P-205 m/z = 838.23(C₅₆H₃₆F₂N₂S₂ = 839.03) P-206 m/z =924.32(C₆₇H₄₄N₂OS = 925.16) P-207 m/z = 999.36(C₇₃H₄₉N₃S = 1000.28)P-208 m/z = 788.23(C₅₅H₃₆N₂S₂ = 789.03) P-209 m/z = 864.26(C₆₁H₄₀N₂S₂ =865.13) P-210 m/z = 847.30(C₆₁H₄₁N₃S = 848.08) P-211 m/z =772.25(C₅₅H₃₆N₂OS = 772.97) P-212 m/z = 887.33(C₆₄H₄₅N₃S = 888.15) P-213m/z = 888.32(C₆₄H₄₄N₂OS = 889.13) P-214 m/z = 972.33(C₇₀H₄₄N₄S = 973.21)P-215 m/z = 924.32(C₆₇H₄₄N₂OS = 925.16) P-216 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-217 m/z = 865.29(C₆₁H₄₀FN₃S = 866.07) P-218 m/z =772.25(C₅₅H₃₆N₂OS = 772.97) P-219 m/z = 844.29(C₅₉H₄₄N₂S₂ = 845.14)P-220 m/z = 845.29(C₆₁H₃₉N₃S = 846.06) P-221 m/z = 848.29(C₆₁H₄₀N₂OS =849.06) P-222 m/z = 786.29(C₅₆H₃₈N₂O₃ = 786.93) P-223 m/z =831.32(C₆₁H₄₁N₃O = 832.02) P-224 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97) P-225m/z = 886.28(C₆₂H₃₈N₄OS = 887.07) P-226 m/z = 756.28(C₅₅H₃₆N₂O₂ =756.91) P-227 m/z = 983.39(C₇₃H₄₉N₃O = 984.22) P-228 m/z =884.38(C₆₃H₅₂N₂OS = 885.18) P-229 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97)P-230 m/z = 983.39(C₇₃H₄₉N₃O = 984.22) P-231 m/z = 908.34(C₆₇H₄₄N₂O₂ =909.10) P-232 m/z = 772.25(C₅₅H₃₆N₂OS = 772.97) P-233 m/z =831.32(C₆₁H₄₁N₃O = 832.02) P-234 m/z = 826.23(C₅₅H₃₃F₃N₂OS = 826.94)P-235 m/z = 756.28(C₅₅H₃₆N₂O₂ = 756.91) P-236 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-237 m/z = 844.31(C₅₉H₄₄N₂O₂S = 845.07) P-238 m/z =849.32(C₆₁H₄₀FN₃O = 850.01) P-239 m/z = 908.34(C₆₇H₄₄N₂O₂ = 909.10)P-240 m/z = 829.31(C₆₁H₃₉N₃O = 830.00) P-241 m/z = 772.25(C₅₅H₃₆N₂OS =772.97) P-242 m/z = 756.28(C₅₅H₃₆N₂O₂ = 756.91) P-243 m/z =772.25(C₅₅H₃₆N₂OS = 772.97) P-244 m/z = 881.34(C₆₅H₄₃N₃O = 882.08) P-245m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-246 m/z = 923.33(C₆₇H₄₅N₃S = 924.18)P-247 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-248 m/z = 832.31(C₆₁H₄₀N₂O₂ =833.00) P-249 m/z = 864.26(C₆₁H₄₀N₂S₂ = 865.13) P-250 m/z =832.31(C₆₁H₄₀N₂O₂ = 833.00) P-251 m/z = 907.36(C₆₇H₄₅N₃O = 908.12) P-252m/z = 864.26(C₆₁H₄₀N₂S₂ = 865.13) P-253 m/z = 923.33(C₆₇H₄₅N₃S = 924.18)P-254 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-255 m/z = 907.36(C₆₇H₄₅N₃O =908.12) P-256 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06) P-257 m/z =848.29(C₆₁H₄₀N₂OS = 849.06) P-258 m/z = 848.29(C₆₁H₄₀N₂OS = 849.06)P-259 m/z = 939.33(C₆₇H₄₅N₃OS = 940.18) P-260 m/z = 939.33(C₆₇H₄₅N₃OS =940.18) P-261 m/z = 838.25(C₅₉H₃₈N₂S₂ = 839.09) P-262 m/z =806.29(C₅₉H₃₈N₂O₂ = 806.97) P-263 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03)P-264 m/z = 822.27(C₅₉H₃₈N₂OS = 823.03) P-265 m/z = 973.35(C₇₁H₄₇N₃S =974.24) P-266 m/z = 882.32(C₆₅H₄₂N₂O₂ = 883.06)

Fabrication and Evaluation of Organic Electric Element [Example 1] RedOrganic Electroluminescent Element (an Emission-Auxiliary Layer)

After vacuum-depositing4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,“2-TNATA”) on an ITO layer (anode) formed on a glass substrate to form ahole injection layer with a thickness of 60 nm, a hole transport layerwith a thickness of 60 nm was formed by vacuum-depositingN,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter, “NPB”) on the hole injection layer.

Subsequently, an emission-auxiliary layer with a thickness of 20 nm wasformed by vacuum-depositing the compound P-1 of the present invention onthe hole transport layer and 4,4′-N,N′-dicarbazole-biphenyl(hereinafter,“CBP”) as a host material andbis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter,“(piq)₂Ir(acac)”) as a dopant material in a weight ratio of 95:5 weredeposited on the emission-auxiliary layer to form a light emitting layerwith a thickness of 30 nm.

Subsequently,(1,1′-bisphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited to a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, andtris-(8-hydroxyquinoline)aluminum (hereinafter, “Alq₃”) wasvacuum-deposited to a thickness of 40 nm on the hole blocking layer toform a an electron transport layer.

Thereafter, LiF was deposited to a thickness of 0.2 nm to form anelectron injection layer, and then Al was deposited to a thickness of150 nm to form a cathode.

[Example 2] to [Example 44]

The organic electroluminescent elements were fabricated in the samemanner as described in Example 1 except that the compounds of thepresent invention described in the following Table 4, instead ofcompound P-1 of the present invention, were used as material of anemission-auxiliary layer.

Comparative Example 11

The organic electroluminescent element was fabricated in the same manneras in Example 1, except that an emission-auxiliary layer was not formed.

[Comparative Example 2] and [Comparative Example 3]

The organic electroluminescent elements were fabricated in the samemanner as described in Example 1 except that Comparative Compound A or Bwere used as material of an emission-auxiliary layer.

Electroluminescence (EL) characteristics were measured with PR-650(Photoresearch) by applying a forward bias DC voltage to the organicelectroluminescent elements prepared in Examples 1 to 44 of the presentinvention and Comparative Examples 1 to 3. And, the T95 life time wasmeasured using a lifetime measuring apparatus manufactured by McscienceInc. at reference brightness of 2500 cd/m². The measurement results areshown in Tables 4 below.

TABLE 4 Voltage Current Density CIE Compound (V) (mA/cm²) Brightness(cd/m²) Efficiency (cd/A) Lifetime T (95) x y comp. Ex (1) — 6.7 34.22500  7.3  62.9 0.61 0.31 comp. Ex (2) comp. Com A 5.8 14.5 2500 17.2 85.0 0.60 0.34 comp. Ex (3) comp. Com B 5.0 10.4 2500 24.0 113.2 0.610.30 Ex. (1) Com. (P-1) 4.8 10.1 2500 24.8 151.4 0.62 0.33 Ex. (2) Com.(P-2) 4.8 9.7 2500 25.8 163.0 0.62 0.33 Ex. (3) Com. (P-4) 4.8 10.6 250023.5 131.6 0.63 0.33 Ex. (4) Com. (P-9) 5.1 10.5 2500 23.7 131.8 0.630.31 Ex. (5) Com. (P-21) 4.9 10.3 2500 24.2 148.6 0.61 0.33 Ex. (6) Com.(P-31) 5.1 10.6 2500 23.6 131.7 0.61 0.35 Ex. (7) Com. (P-33) 4.8 10.22500 24.5 149.9 0.64 0.34 Ex. (8) Com. (P-41) 4.8 8.9 2500 28.0 177.70.64 0.32 Ex. (9) Com. (P-42) 4.8 9.5 2500 26.4 161.9 0.61 0.35 Ex. (10)Com. (P-44) 4.9 9.1 2500 27.4 174.4 0.60 0.32 Ex. (11) Com. (P-45) 4.89.2 2500 27.2 172.7 0.61 0.34 Ex. (12) Com. (P-50) 4.9 9.1 2500 27.5174.4 0.65 0.34 Ex. (13) Com. (P-59) 4.9 10.8 2500 23.1 129.2 0.62 0.32Ex. (14) Com. (P-64) 4.8 11.0 2500 22.8 127.9 0.63 0.31 Ex. (15) Com.(P-70) 4.9 9.6 2500 25.9 164.7 0.65 0.32 Ex. (16) Com. (P-83) 5.0 10.92500 22.9 134.3 0.63 0.33 Ex. (17) Com. (P-89) 5.3 10.7 2500 23.4 151.50.63 0.31 Ex. (18) Com. (P-106) 5.1 10.2 2500 24.4 157.6 0.62 0.34 Ex.(19) Com. (P-112) 5.1 9.7 2500 25.7 171.1 0.63 0.33 Ex. (20) Com.(P-117) 5.1 9.8 2500 25.4 149.2 0.61 0.34 Ex. (21) Com. (P-118) 5.2 10.02500 25.0 147.9 0.64 0.34 Ex. (22) Com. (P-131) 5.1 10.3 2500 24.3 142.40.61 0.31 Ex. (23) Com. (P-132) 5.2 9.9 2500 25.1 167.7 0.63 0.31 Ex.(24) Com. (P-138) 5.0 9.9 2500 25.3 167.9 0.60 0.32 Ex. (25) Com.(P-141) 5.1 9.7 2500 25.7 165.3 0.61 0.34 Ex. (26) Com. (P-145) 5.1 10.12500 24.7 159.1 0.61 0.30 Ex. (27) Com. (P-148) 5.2 10.6 2500 23.6 138.30.61 0.31 Ex. (28) Com. (P-162) 4.8 9.2 2500 27.1 172.5 0.63 0.34 Ex.(29) Com. (P-192) 5.0 9.9 2500 25.2 140.9 0.61 0.34 Ex. (30) Com.(P-195) 5.3 9.3 2500 27.0 181.4 0.61 0.30 Ex. (31) Com. (P-196) 5.0 10.22500 24.6 156.0 0.62 0.31 Ex. (32) Com. (P-204) 4.9 9.8 2500 25.6 148.80.61 0.31 Ex. (33) Com. (P-208) 4.9 10.0 2500 25.1 148.5 0.63 0.31 Ex.(34) Com. (P-211) 5.0 9.7 2500 25.9 164.5 0.62 0.33 Ex. (35) Com.(P-216) 4.9 9.0 2500 27.7 166.3 0.60 0.34 Ex. (36) Com. (P-220) 5.0 11.02500 22.8 127.8 0.61 0.34 Ex. (37) Com. (P-223) 5.2 10.9 2500 22.9 134.40.63 0.34 Ex. (38) Com. (P-226) 5.1 9.2 2500 27.3 171.1 0.63 0.33 Ex.(39) Com. (P-243) 5.2 10.6 2500 23.6 151.4 0.61 0.31 Ex. (40) Com.(P-248) 5.2 9.1 2500 27.5 173.0 0.65 0.31 Ex. (41) Com. (P-250) 5.3 9.52500 26.4 171.3 0.64 0.31 Ex. (42) Com. (P-251) 5.3 10.6 2500 23.5 138.30.63 0.32 Ex. (43) Com. (P-254) 5.0 8.9 2500 28.1 168.0 0.62 0.32 Ex.(44) Com. (P-262) 5.1 9.4 2500 26.6 167.8 0.61 0.34As can be seen from the results of Table 4, when a red organicelectroluminescent device was manufactured with the compounds of thepresent invention as material for an emission-auxiliary layer, lifetimecan be improved, compared to Comparative Example 1 having noemission-auxiliary layer, or Comparative Examples 2 and 3 prepared withComparative Compound A or Comparative Compound B as material for anemission-auxiliary layer.

The results from Comparative Example 2 or Comparative Example 3 preparedwith Comparative Compound A or Comparative Compound B are superior toComparative Example 1 having no emission-auxiliary layer, and it can beseen that Example 1 to Example 44 of the present invention areremarkably superior in lifetime.

Table 5 below shows the physical property values of Compound P-45 of thepresent invention, Comparative Compound A, Comparative Compound B, andNPB.

TABLE 5 Compound Compound P-45 comp. ComA comp. ComB NPB G. HOMO −4.84−4.67 −4.87 −4.71 G. LUMO −1.00 −0.99 −1.14 −1.12 G. Band Gap 3.84 3.683.73 3.59

Comparing the compound of the present invention with ComparativeCompound A, the linking group between the amino groups is carbazole inComparative Compound A, while dibenzofuran and dibenzothiophene areintroduced as the linking group in the compound of the presentinvention.

As can be seen in Table 5, where carbazole is introduced as a linker(Comparative Compound A), the HOMO value is higher than that of thecompound of the present invention in which dibenzofuran ordibenzothiophene is introduced, and has a higher HOMO value than the NPBused as a material for the hole transport layer in Example 1.

Therefore, in the case of Comparative Compound A, the hole is not easilymoved to the host, compared to the compound of the present invention,and the hole is accumulated. As a result, the charge balance in thelight emitting layer is decreased, so that the efficiency and lifetimeare significantly lower than the compound of the present invention.

Comparing the compound of the present invention with ComparativeCompound B, Comparative compound B has the structure in whichdibenzofuran is introduced as a substituent of an amino group, whilespiro[fluorene-9,9′-xanthene], spiro[fluorene-9,9′-thioxanthene],spiro[acridine-9,9′-fluorene], etc. are introduced as substituents inthe compound of the present invention.

As can be seen from Table 5, the compound of the present invention has ahigher LUMO value than Comparative Compound B in which dibenzofuran issubstituted, so that electrons moving from the host to the holetransport layer can be more effectively blocked. Therefore, damage tothe hole transport layer or the emission-auxiliary layer can beminimized, and as a result the lifetime seems significantly improved.

In the case of the emission-auxiliary layer, it will be very difficultfor a person of ordinary skill in the art to infer/expect thecharacteristics exhibited in the case where the compound of the presentinvention is used for the emission-auxiliary layer, even from the casewhere a similar core compound is used, because the relationship betweenthe hole transport layer and the light-emitting layer (host) needs to beunderstood.

In addition, in the evaluation results of the above-mentioned elementfabrication, although the characteristics of the element are describedwith the case where the compound of the present invention is applied foran emission-auxiliary layer, the compound of the present invention canbe also applied to a hole transport layer or to both a hole transportlayer and an emission-auxiliary layer.

Although the exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art to whichthe present invention pertains will be capable of various modificationswithout departing from the essential characteristics of the presentinvention. Therefore, the embodiment disclosed herein is intended toillustrate the scope of the technical idea of the present invention, andthe spirit and scope of the present invention are not limited by theembodiments. The scope of the present invention shall be construed onthe basis of the accompanying claims, and it shall be construed that allof the technical ideas included within the scope equivalent to theclaims belong to the present invention.

1. A compound of Formula 1:

wherein: Ar¹ to Ar⁶ are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, a C₃-C₆₀ aliphatic ring group, -L′-N(R_(a))(R_(b)), Formula A-1and Formula A-2, and at least one of Ar¹ to Ar⁶ is Formula A-1 orFormula A-2,

X¹ is O or S, X² is N(R′), O or S, R¹ to R⁶ are each independentlyselected from the group consisting of hydrogen, deuterium, halogen,cyano group, nitro group, a C₆-C₆₀ aryl group, a fluorenyl group, aC₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S,Si, and P, a C₃-C₆₀ aliphatic ring group, a C₁-C₃₀ alkyl group, a C₂-C₃₀alkenyl group, a C₂-C₃₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀aryloxy group and -L′-N(R_(a))(R_(b)), and adjacent groups together maybe bonded to each other to form a ring, n, p′ and r′ are each an integerof 0 to 3, m, o, p, q and r are each an integer of 0 to 4, and wherethey are each an integer of 2 to 4, each of R¹s, each of R²s, each ofR³s, each of R⁴s, each of R⁵s, or each of R⁶s is the same or differentfrom each other, x and y are each an integer of 0 to 2, and x+y is aninteger greater than or equal to 1, L¹ to L³ and L′ are eachindependently selected from the group consisting of a single bond, aC₆-C₆₀ arylene group, a fluorenylene group, a C₃-C₆₀ aliphatic ringgroup and a C₂-C₆₀ heterocyclic group containing at least one heteroatomof O, N, S, Si, and P, R′, R_(a) and R_(b) are each independentlyselected from the group consisting of a C₆-C₆₀ aryl group, a fluorenylgroup, a C₂-C₆₀ heterocyclic group containing at least one heteroatom ofO, N, S, Si, and P and a C₃-C₆₀ aliphatic ring group, Ar¹ to Ar⁶, R¹ toR⁶, L¹ to L³, R′ and the ring formed by adjacent groups may be eachoptionally substituted with one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aC₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group, a C₆-C₂₀ aryloxy group,a C₆-C₂₀ arylthio group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group, andC₈-C₂₀ arylalkenyl group.
 2. The compound of claim 1, wherein Formula 1is represented by Formula 2 or Formula 3:

wherein X¹, L¹-L³, Ar¹-Ar⁶, R, R², n and m are the same as defined inclaim
 1. 3. The compound of claim 1, wherein Formula 1 is represented byone of Formula 4 to Formula 19:

wherein X¹, L¹-L³, Ar¹-Ar⁶, R¹, R², n and m are the same as defined inclaim
 1. 4. The compound of claim 1, wherein Formula 1 is represented byone of Formula 20 to Formula 34:

wherein X¹, L¹-L³, Ar¹-Ar⁶, R¹, R², n and m are the same as defined inclaim
 1. 5. The compound of claim 1, wherein at least one of L¹ to L³ isa single bond.
 6. The compound of claim 1, wherein the compoundrepresented by Formula 1 is one of the following compounds:


7. An organic electric element comprising an anode, a cathode, and anorganic material layer formed between the anode and the cathode, whereinthe organic material layer comprises a single compound or a mixture oftwo or more compounds represented by Formula 1 of claim
 1. 8. An organicelectric element comprising an anode, a cathode, an organic materiallayer formed between the anode and the cathode, and a layer forimproving luminous efficiency, wherein the layer for improving luminousefficiency is formed on one side of the anode and/or the cathode, theone side not facing the organic material layer, and the organic materiallayer or the layer for improving luminous efficiency comprises a singlecompound or a mixture of two or more compounds represented by Formula 1of claim
 1. 9. The organic electric element of claim 7, wherein theorganic material layer comprises at least one of a hole injection layer,a hole transport layer, an emission-auxiliary layer, a light emittinglayer, an electron transport-auxiliary layer, an electron transportlayer and an electron injection layer.
 10. The organic electric elementof claim 9, wherein the compound is comprised in the emission-auxiliarylayer.
 11. The organic electric element of claim 7, wherein the organicmaterial layer comprises two or more stacks and the stacks comprise thehole transport layer, the light emitting layer and the electrontransport layer formed sequentially on the anode.
 12. The organicelectric element of claim 11, wherein the organic electric elementfurther comprises the charge generation layer formed between the stacks.13. An electronic device comprising a display device and a control unitfor driving the display device, wherein the display device comprises theorganic electric element of claim
 7. 14. The electronic device of claim13, wherein the organic electric element is selected from the groupconsisting of an organic electroluminescent element, an organic solarcell, an organic photo conductor, an organic transistor, an element formonochromatic illumination and an element for quantum dot display. 15.The organic electric element of claim 8, wherein the organic materiallayer comprises at least one of a hole injection layer, a hole transportlayer, an emission-auxiliary layer, a light emitting layer, an electrontransport-auxiliary layer, an electron transport layer and an electroninjection layer.
 16. The organic electric element of claim 15, whereinthe compound is comprised in the emission-auxiliary layer.
 17. Theorganic electric element of claim 8, wherein the organic material layercomprises two or more stacks and the stacks comprise the hole transportlayer, the light emitting layer and the electron transport layer formedsequentially on the anode.
 18. The organic electric element of claim 17,wherein the organic electric element further comprises the chargegeneration layer formed between the stacks.
 19. An electronic devicecomprising a display device and a control unit for driving the displaydevice, wherein the display device comprises the organic electricelement of claim
 8. 20. The electronic device of claim 19, wherein theorganic electric element is selected from the group consisting of anorganic electroluminescent element, an organic solar cell, an organicphoto conductor, an organic transistor, an element for monochromaticillumination and an element for quantum dot display.